CSJ Journal Report Vol. 1 Contents Analytical Chemistry — — 01 Asymmetric Catalysis — — 04 Chemical Biology — — 05 Coordination Chemistry — — 08 Efficient Synthesis — — 09 Innovative Materials — — 16 Mesoporous Materials — — 25 Metal Catalysis — — 26 Nanotechnology — — 31 Novel Bonding and Structures — — 34 Organic Electronics — — 36 Photochemistry — — 38 Physical Analysis — — 39 Supramolecules — — 41 Theoretical Chemistry — — 44 Analytical Chemistry NMR Tools for Oligosaccharides Open Access doi: 10.1246/cl.130789 Highlight Review New NMR Tools for Characterizing the Dynamic Conformations and Interactions of Oligosaccharides K. Kato Ying Zhang, Takumi Yamaguchi, and Koichi Kato Chem. Lett. 2013, 42, 1455–1462. Turn-on Sensing of Enzyme Activity Open Access doi: 10.1246/cl.130697 Editor’s Choice Disassembly-driven Turn-on Sensing of Enzyme Activity by Substrate-based Fluorescent Nanoprobe I. Hamachi Yousuke Takaoka, Yoshiaki Fukuyama, Kazuya Matsuo, and Itaru Hamachi Chem. Lett. 2013, 42, 1426–1428. Phosphorus Porphyrins Open Access doi: 10.1246/bcsj.20130191 BCSJ Award Article Spectroscopic Analysis of the Interaction of Human Serum Albumin with Tricationic Phosphorus Porphyrins Bearing Axial Pyridinio Groups J. Matsumoto Ph O Laser Ablation of Molecular Systems Open Access C6H13 Ph N N P N N Ph Jin Matsumoto, Tomoya Kubo, Tomohiko Shinbara, Naomi Matsuda, Tsutomu Shiragami, Mamoru Fujitsuka, Tetsuro Majima, and Masahide Yasuda Bull. Chem. Soc. Jpn. 2013, 86, 1240–1247. Br N O Cl Ph O O N Br C6H13 High water solubility High affinity to HSA Award Accounts doi: 10.1246/bcsj.20130066 Time-Resolved Spectroscopic and Imaging Studies on Laser Ablation of Molecular Systems: From Mechanistic Study to Bio/Nano Applications H. Masuhara Hiroshi Masuhara Bull. Chem. Soc. Jpn. 2013, 86, 755–783. MALDI Crystals Open Access doi: 10.1246/cl.121232 Editor’s Choice Settlement of the Sweet-spot Problem of MALDI Crystals Using Cyclodextrinsupported Matrix T. Fujino Takashi Fujita and Tatsuya Fujino Chem. Lett. 2013, 42, 350–351. −1− CSJ Journal Report Vol. 1 Circular Dichroism Spectroscopy Open Access doi: 10.1246/cl.2013.261 Editor’s Choice Remarkable Enhancement of Sensitivity with the Second Generation of Elliptically Polarization-detected Circular Dichroism Spectroscopy T. Wada Makoto Murakami, Yasuyuki Araki, Seiji Sakamoto, Yoshiki Hamada, and Takehiko Wada Chem. Lett. 2013, 42, 261–262. DNA Separation Open Access doi: 10.1246/cl.2012.1506 Editor’s Choice Effect of Temperature on DNA Chromatographic Separation in Free Solution 80°C 70°C 60°C 50°C X. Wang 40°C Ruonan Li, Lei Liu, Yu Wang, and Xiayan Wang Chem. Lett. 2012, 41, 1506–1508. Purification of Pinacol Boronic Esters Open Access 25°C 25 30 35 40 45 50 55 60 65 70 75 Retention Time/min Editor’s Choice doi: 10.1246/cl.2012.972 A Facile Chromatographic Method for Purification of Pinacol Boronic Esters H. Isobe Shunpei Hitosugi, Daiki Tanimoto, Waka Nakanishi, and Hiroyuki Isobe Chem. Lett. 2012, 41, 972–973. Iron(III) and Manganese(III) Salen Complexes Open Access BCSJ Award Article doi: 10.1246/bcsj.20120146 Comparative Spectroscopic Studies of Iron(III) and Manganese(III) Salen Complexes Having a Weakly Coordinating Triflate Axial Ligand H. Fujii Takuya Kurahashi and Hiroshi Fujii Bull. Chem. Soc. Jpn. 2012, 85, 940–947. Enantioseparation Open Access doi: 10.1246/cl.2012.809 Editor’s Choice Enantioseparation on Helical Poly(phenylacetylene)s Bearing Cinchona Alkaloid Pendants as Chiral Stationary Phases for HPLC E. Yashima Yuki Naito, Zhenglin Tang, Hiroki Iida, Toshitaka Miyabe, and Eiji Yashima Chem. Lett. 2012, 41, 809–811. CSJ Journal Report Vol. 1 −2− Fixation of Cesium Ions Open Access doi: 10.1246/cl.2012.380 Editor’s Choice XRD and HRTEM Evidence for Fixation of Cesium Ions in Vermiculite Clay H. Sato Toshihiro Kogure, Kazuya Morimoto, Kenji Tamura, Hisako Sato, and Akihiko Yamagishi Chem. Lett. 2012, 41, 380–382. Sulfuric Acid Solution Open Access doi: 10.1246/cl.2012.159 Editor’s Choice Small- and Large-angle X-ray Scattering Studies of Nanometer-order Sulfuric Acid Solution in Carbon Micropores R. Futamura Ryusuke Futamura, Taku Iiyama, Atom Hamasaki, and Sumio Ozeki Chem. Lett. 2012, 41, 159–161. Separation of Cesium Ion doi: 10.1246/cl.2012.32 Letter Magnetic Separation of Cesium Ion Using Prussian Blue Modified Magnetite S. Tanaka Takahiro Sasaki and Shunitz Tanaka Chem. Lett. 2012, 41, 32–34. −3− CSJ Journal Report Vol. 1 Asymmetric Catalysis Diazocarbonyl Compounds in Acid Catalysis Open Access doi: 10.1246/bcsj.20130164 Award Accounts nucleophilic in acid catalysis Development of Synthetic Transformations by Control of Acid-Catalyzed Reactions of Diazocarbonyl Compounds O COX R T. Hashimoto N2 Takuya Hashimoto and Keiji Maruoka Bull. Chem. Soc. Jpn. 2013, 86, 1217–1230. C–F Bond Breaking Open Access R = X N N doi: 10.1246/bcsj.20120359 BCSJ Award Article C–F Bond Breaking through Aromatic Nucleophilic Substitution with a Hydroxo Ligand Mediated via Water Bifunctional Activation T. Ikariya Pavel A. Dub, Hui Wang, Asuka Matsunami, Ilya D. Gridnev, Shigeki Kuwata, and Takao Ikariya Bull. Chem. Soc. Jpn. 2013, 86, 557–568. Pd-Catalyzed Intermolecular Cyclization Open Access γ-Methylidene-δ-valerolactones: New Reagents for Palladium-Catalyzed Intermolecular Cyclization Reactions R. Shintani δ– O Ryo Shintani Bull. Chem. Soc. Jpn. 2012, 85, 931–939. CSJ Journal Report Vol. 1 doi: 10.1246/bcsj.20120171 Award Accounts R −4− O Pd(0) CO2R' – CO2 Pd(II) δ+ – Pd(0) R CO2R' R CO2R' Chemical Biology Hydrolytic Antibodies Open Access doi: 10.1246/cl.131220 Highlight Review Directed Evolution of Hydrolytic Antibodies in Phage-displayed Combinatorial Libraries I. Fujii H N O O2 N HN OH HN O2 N O O2N H N O O CF3 O OH CHCl2 HN CHCl2 O O TSA Open Access OH OH CHCl2 O Takeshi Tsumuraya and Ikuo Fujii Chem. Lett. 2014, 43, 272–280. Phototoxicity of Chlorophylls CF3 O O O H N O O2 N CH3 O O OH CHCl2 HN O Newly devised TSA used for panning doi: 10.1246/cl.131005 Highlight Review Risk Management by Organisms of the Phototoxicity of Chlorophylls H. Tamiaki Yuichiro Kashiyama and Hitoshi Tamiaki Chem. Lett. 2014, 43, 148–156. Organometallic DNA Open Access doi: 10.1246/cl.131019 Highlight Review Metal–Carbon Bonds in Biopolymer Conjugates: Bioorganometallic Nucleic Acid Chemistry J. H. R. Tucker Open Access P O- Jean-Louis H. A. Duprey and James H. R. Tucker Chem. Lett. 2014, 43,157–163. Drug-Like Peptides O O -O POSTSYNTHETIC INCORPORATION M O P O O O- P O O- ENZYMATIC INCORPORATION CHEMICAL OLIGOMERIZATION doi: 10.1246/cl.130910 Highlight Review Flexizymes-facilitated Genetic Code Reprogramming Leading to the Discovery of Drug-like Peptides H. Suga Naohiro Terasaka and Hiroaki Suga Chem. Lett. 2014, 43, 11–19. Protein Allostery Open Access doi: 10.1246/cl.130965 Highlight Review Insights into Protein Allostery in the CsoR/RcnR Family of Transcriptional Repressors D. Giedroc Khadine A. Higgins and David Giedroc Chem. Lett. 2014, 43, 20–25. −5− CSJ Journal Report Vol. 1 Nitrogenase Metallo-Clusters Open Access doi: 10.1246/bcsj.20130207 Award Accounts Synthetic Analogues of the Active Sites of Nitrogenase and [NiFe] Hydrogenase S Nitrogenase Fe Fe S Fe Fe Fe Fe Yasuhiro Ohki Bull. Chem. Soc. Jpn. 2014, 87, 1–19. Fe [NiFe] hydrogenase S Fe Mo Fe S S FeMo-cofactor CO Cys S Fe Ni S CN S CO Fe – Ni CN CN Fe S Fe Fe S Fe C Fe S Fe P-cluster S Y. Ohki S S Cys CO CN S CO Fe S CO CO Ni S S [NiFe] hydrogenase Chemicals-Inspired Biomaterials Open Access Award Accounts doi: 10.1246/bcsj.20130182 Chemicals-Inspired Biomaterials: Developing Biomaterials Inspired by Material Science Based on POSS K. Tanaka Kazuo Tanaka and Yoshiki Chujo Bull. Chem. Soc. Jpn. 2013, 86, 1231–1239. DNA-Conjugated Polymers Open Access doi: 10.1246/bcsj.20130038 Award Accounts DNA-Conjugated Polymers for Reliable SNP Genotyping Based on Affinity Capillary Electrophoresis M. Maeda Tohru Takarada and Mizuo Maeda Bull. Chem. Soc. Jpn. 2013, 86, 547–556. Monoclonal Antibody Open Access doi: 10.1246/bcsj.20120253 BCSJ Award Article Development and Characterization of a Monoclonal Antibody against Triacetone Triperoxide T. Matsumoto Toru Matsumoto, Hiroyasu Yamaguchi, Ken’ichi Kamijo, Miyako Akiyoshi, Takehiro Matsunaga, and Akira Harada Bull. Chem. Soc. Jpn. 2013, 86, 198–202. Kinetics of Charge Transfer through DNA Open Access BCSJ Award Article Kinetics of Charge Transfer through DNA across Guanine–Cytosine Repeats Intervened by Adenine–Thymine Base Pair(s) K. Kawai Yasuko Osakada, Kiyohiko Kawai, and Tetsuro Majima Bull. Chem. Soc. Jpn. 2013, 86, 25–30. CSJ Journal Report Vol. 1 −6− doi: 10.1246/bcsj.20120224 Venomous Mammals and Marine Invertebrates Open Access doi: 10.1246/bcsj.20120198 Award Accounts Bioorganic Studies on the Key Natural Products from Venomous Mammals and Marine Invertebrates M. Kita Masaki Kita Bull. Chem. Soc. Jpn. 2012, 85, 1175–1185. Chemical Biology of Natural Products Open Access doi: 10.1246/cl.2012.658 Highlight Review Chemical Biology of Natural Products on the Basis of Identification of Target Proteins M. Ueda “Lock” A Minoru Ueda Chem. Lett. 2012, 41, 658–666. “Lock” B Artificial Restriction DNA Cutters Open Access “Lock” C doi: 10.1246/bcsj.20110318 Award Accounts Design and Applications of Artificial Restriction DNA Cutters for Site-Selective Scission of Genomes pcPNA strands Ce Ce(IV)/EDTA Ce Scission M. Komiyama Cytochrome c Oxidase T. Ogura Scission Makoto Komiyama and Jun Sumaoka Bull. Chem. Soc. Jpn. 2012, 85, 533–544. Open Access Ce doi: 10.1246/cl.2012.178 Editor’s Choice An Intermediate Conformational State during Ligand Binding to Cytochrome c Oxidase Detected by Time-resolved Resonance Raman Analyses of Heme Peripheral Groups Izumi Ishigami, Takeshi Nishigaki, Kyoko Shinzawa-Itoh, Shinya Yoshikawa, Satoru Nakashima, and Takashi Ogura Chem. Lett. 2012, 41, 178–180. Photosynthesis doi: 10.1246/cl.2012.18 Letter Effectiveness of Optimizing Geometry for CaMn4O5 Cluster at 1.9 Å Resolved OEC and Proposal for Oxidation Mechanism from S0 to S3 States Tyr161 W4 W5 Y. Yoshioka W2 Mn4 W8 Tomoya Ichino, Kizashi Yamaguchi, and Yasunori Yoshioka Chem. Lett. 2012, 41,18–20. W9 O2 W7 −7− Mn2 O1 O5 O4 W1 Asp61 W3 Mn3 W6 O3 Glu189 Mn1 CSJ Journal Report Vol. 1 Coordination Chemistry Luminescent Complexes Open Access doi: 10.1246/cl.2013.204 Highlight Review Luminescent Complexes Containing Halogeno-bridged Dicopper(I) Unit {Cu2(µ-X)2} (X = Cl, Br, and I) K. Tsuge Ph3P Kiyoshi Tsuge Chem. Lett. 2013, 42, 204–208. X L Cu L Cu X PPh3 Luminescence of complexes with {Cu2 X2} unit Platinum–Silyl Complexes Open Access doi: 10.1246/cl.2012.1538 Editor’s Choice Formation of Unique Platinum–Silyl Complexes by the Reactions of a Zero-valent Platinum Complex with Various Trisilanes 0H6L 3 K. Mochida 3 Hidekazu Arii, Makiko Takahashi, Hideyuki Takahashi, Kunio Mochida, and Takayuki Kawashima Chem. Lett. 2012, 41, 1538–1540. Si–H Bond Activation H. Tobita Open Access 3W 6L 6L+0H 6L0H 6L 3W 6L+0H 3 3 3 33K 6L+0H 6L+0H 3K 3 3W 3 3K 6L0H 6L+0H 3K 6L+0H 3 3W 3 6L+0H 3K doi: 10.1246/cl.2012.774 Editor’s Choice Silane(silyl) and Bis(silyl)hydrido Manganese Complexes with Different Mn···H···Si Interaction: Observation of Gradual Si–H Bond Activation on the Metal Center Takashi Komuro, Satoshi Okawara, Keisuke Furuyama, and Hiromi Tobita Chem. Lett. 2012, 41, 774–776. Organoruthenium(0) Complex Open Access doi: 10.1246/cl.2012.650 Editor’s Choice A Neutral Five-coordinated Organoruthenium(0) Complex: X-ray Structure and Unique Solvatochromism H. Nakai Kihun Jeong, Harutaka Nakamori, Shunsuke Imai, Takahiro Matsumoto, Seiji Ogo, and Hidetaka Nakai Chem. Lett. 2012, 41, 650–651. CSJ Journal Report Vol. 1 / −8− Efficient Synthesis C–H Bond Functionalization Open Access doi: 10.1246/cl.131154 Highlight Review Alcohols or Masked Alcohols as Directing Groups for C–H Bond Functionalization G. Dong OH C– H Functionalization OH R Fanyang Mo, John R. Tabor, and Guangbin Dong Chem. Lett. 2014, 43, 264–271. 1 H R2 DG O or n H M cat R2 R1 n n O R1 Buckybowls Bearing Electron-withdrawing Groups Open Access FG R2 R1 FG R2 n doi: 10.1246/cl.130984 Highlight Review Syntheses and Properties of Buckybowls Bearing Electron-withdrawing Groups D. Lentz Bernd M. Schmidt and Dieter Lentz Chem. Lett. 2014, 43, 171–177. Novel Cyclization Reaction Open Access doi: 10.1246/bcsj.20130216 Award Accounts An Adventurous Synthetic Journey with MNBA from Its Reaction Chemistry to the Total Synthesis of Natural Products MNBA DMAP (cat.) OH O R OH O O Et3N R β-Lactone Seco-acid MNBA, DMAP – DMAP R I. Shiina Isamu Shiina Bull. Chem. Soc. Jpn. 2014, 87, 196–233. O O N Me N H H O Me H O O2N Me Transition State Mukaiyama Aldol Reactions Open Access doi: 10.1246/cl.130920 Highlight Review The Chelation-controlled Mukaiyama Aldol Reaction of Chiral α- and β-Alkoxy Aldehydes M. T. Reetz Gheorghe-Doru Roiban, Adriana Ilie, and Manfred T. Reetz Chem. Lett. 2014, 43, 2–10. Ethynylated Anthracene Bisimides Open Access BnO R1 OSiMe 3 + H R1 O + OBn H bicoordinate R2 Lewis acid OSiMe 3 bicoordinate R 2 BnO OH R1 O R2 R1 Lewis acid R2 OBn OH O doi: 10.1246/cl.130842 Editor’s Choice Introduction of an Arylethynyl Group onto an Anthracene Bisimide Core for Molecular Design of New π-Conjugated Compounds S. Toyota O O Anthracene donor O O R N Tetsuo Iwanaga, Ryo Tanaka, and Shinji Toyota Chem. Lett. 2014, 43, 105–107. O −9− N R O O R N N R O R N O ABI unit O N R O O O O O Extended π-conjugation by arylethynyl group R N O N R O CSJ Journal Report Vol. 1 Titania and Zirconia Nanosheets Open Access doi: 10.1246/cl.130587 Editor’s Choice Bottom-up Synthesis of Titania and Zirconia Nanosheets and Their Composites with Graphene S. Takenaka Sakae Takenaka, Shunsuke Uwai, Shintaro Ida, Hideki Matsune, and Masahiro Kishida Chem. Lett. 2013, 42, 1188–1190. Doyle–Kirmse Reaction Open Access doi: 10.1246/cl.130521 Editor’s Choice Doyle–Kirmse Reaction Using Triazoles Leading to One-pot Multifunctionalization of Terminal Alkynes 5 & & + M. Murakami Tomoya Miura, Takamasa Tanaka, Akira Yada, and Masahiro Murakami Chem. Lett. 2013, 42, 1308–1310. C–N Bond Cleavage Open Access FDW>5K@ HC 2+ CH Fe Fe Fe Fe r.t., 30 min N Fe Fe Fe C HC N C N N doi: 10.1246/cl.130295 O R1 O O N O 1a R1 3 N Cl N H N O OH CF3 1a OH O O (R2 = OPh) CF3 N Me OMe 4 CF3 Me up to 98 % ee O R1 F3C O 4 R2 = OPh or alkyl O R2 (5 mol%) R2 + Cl 8 O (+)-crobarbatic acid 6 O chiral γ -butenolide doi: 10.1246/cl.130504 Highlight Review 1,3-Dipolar Cycloaddition-based Synthesis of Diverse Heterocyclic Scaffolds O R1 R3 N R2 − 10 − NH O R4 O R1 O N O CO2 R NH O N N R3 R1 R2' R2 O R3 R2 O N O Wei Zhang Chem. Lett. 2013, 42, 676–681. CSJ Journal Report Vol. 1 N + CH Fe + – 2 W. Zhang + HC N C C HC Nari Jin, Tomonori Misaki, and Takashi Sugimura Chem. Lett. 2013, 42, 894–896. Open Access 1 'R\OH.LUPVH Editor’s Choice 1,4-Addition Reaction of 5H-Oxazol4-ones to Allenic Esters and Ketones Catalyzed by Chiral Guanidines 1,3-Dipolar Cycloaddition 5 & & doi: 10.1246/cl.130337 Wataru Taniwaki and Masaaki Okazaki Chem. Lett. 2013, 42, 807–809. T. Misaki 63K 17V Editor’s Choice M. Okazaki Open Access FDW>&X@ F\FORDGGLWLRQ C(sp3)–N(sp) Bond Cleavage of Isocyanides at a Cationic [CCH] Subunit in a Bisdisphenoidal Eight-atom Tetrairon–Tetracarbon Cluster Organic Catalysts 63K 7V1 R3' R2 [3+2] adducts N R3 R1 O N O O R1 CO 2R O N R3 N O R4 H O R2 Enantioselective Synthesis K. Soai Open Access doi: 10.1246/cl.130185 Editor’s Choice Enantioselective Synthesis Induced by the Helical Molecular Arrangement in the Chiral Crystal of Achiral Tris(2-hydroxyethyl) 1,3,5-Benzenetricarboxylate in Conjunction with Asymmetric Autocatalysis Asymmetric Autocatalysis Right−handed P −crystal CD(+)224KBr CO2R1 N Open Access S N OH > 99.5% ee N R2 R1O2C CO2R1 Left−handed M −crystal R1 = −CH2CH2OH CD(–)224KBr CHO + i −Pr2Zn R2 = t −Bu−C≡C− N R R2 Asymmetric Autocatalysis Tsuneomi Kawasaki, Mizuki Uchida, Yoshiyasu Kaimori, Taisuke Sasagawa, Arimasa Matsumoto, and Kenso Soai Chem. Lett. 2013, 42, 711–713. Lateral π-Expansion of Bisanthenes N R2 N OH > 99.5% ee doi: 10.1246/cl.130153 Editor’s Choice Facile Synthesis and Lateral π-Expansion of Bisanthenes T. Kubo Akihito Konishi, Yasukazu Hirao, Kouzou Matsumoto, Hiroyuki Kurata, and Takashi Kubo Chem. Lett. 2013, 42, 592–594. Sequential Peptide Ligation T. Kawakami Open Access Direct Cyclization Lateral π -expansion Scholl reaction DDQ, Sc(OTf)3, acid Diels-Alder reaction doi: 10.1246/bcsj.20130026 BCSJ Award Article Sequential Peptide Ligation by Combining the Cys–Pro Ester (CPE) and Thioester Methods and Its Application to the Synthesis of Histone H3 Containing a Trimethyl Lysine Residue peptide B -CO-CPE Open Access Cys- peptide C NCL peptide A -CO-CPE Toru Kawakami, Yuichi Akai, Hisao Fujimoto, Chieko Kita, Yuko Aoki, Takehiko Konishi, Masazumi Waseda, Lisa Takemura, and Saburo Aimoto Bull. Chem. Soc. Jpn. 2013, 86, 690–697. ortho-Linked Oligoarenes π π peptide B -CO-Cys- peptide C Thioester Method peptide A -CO- peptide B -CO-Cys- peptide C doi: 10.1246/cl.130136 Editor’s Choice Anthranilamide-masked o-Iodoarylboronic Acids as Coupling Modules for Iterative Synthesis of ortho-Linked Oligoarenes R HN B NH M. Suginome O Masashi Koyanagi, Nils Eichenauer, Hideki Ihara, Takeshi Yamamoto, and Michinori Suginome Chem. Lett. 2013, 42, 541–543. B(aam) R ortho SiR'3 silylation [Ru] B(aam) B(aam) ICl iodo desilylation R I B(aam) "coupling module" − 11 − R4 H iterative coupling R 3 R2 R1 B(aam) oligo(o -arene)s CSJ Journal Report Vol. 1 Metal Cluster Open Access doi: 10.1246/cl.121227 Editor’s Choice Needle-like NaNbO3 Synthesis via Nb6O198− Cluster Using Na3NbO4 Precursor by Dissolution–Precipitation Method 6KDSHOHVV 1HHGOHOLNH Seiji Yamazoe, Kengo Shibata, Kazuo Kato, and Takahiro Wada Chem. Lett. 2013, 42, 380–382. Open Access &DOFLQDWLRQ DW$& 1E2LRQ S. Yamazoe Azadiradione 1HHGOHOLNH 'LVVROXWLRQ SUHFLSLWDWLRQ PHWKRG 1D1E2 1D1E2 1D +21E2Ã+ 2 doi: 10.1246/cl.2013.220 Editor’s Choice Concise Synthesis of the Tetracyclic Framework of Azadiradione: Tandem Radical Cyclization Route C Mn(OAc)3 S. Yamashita Shuji Yamashita, Akito Naruko, Takahiro Yamada, Yujiro Hayashi, and Masahiro Hirama Chem. Lett. 2013, 42, 220–221. Enantioselective Catalytic Reduction Open Access O Cl O OEt P enhancement M O CH3 Ph O B CH3 BH3•THF in THF 30 °C OH H3C M OH Conventional: 86% yield, 92% ee / 4320 min CH3 Microwave: Reaction Acceleration 82% yield, 91% ee / 20 min doi: 10.1246/bcsj.20120162 BCSJ Award Article spiroacetalization O O O crotylboration O O OR auripyrone A : R = O auripyrone B : R = 2' * aldol-type reaction of γ -pyrone Editor’s Choice Shouta Mizuno, Mika Kurosawa, Masashi Tanaka, and Masakazu Iwamoto Chem. Lett. 2012, 41, 892–894. CSJ Journal Report Vol. 1 cis H OEt Keeping high enantioselectivity!! One-path and Selective Conversion of Ethanol to Propene on Scandiummodified Indium Oxide Catalysts M. Iwamoto H3C CH3 Microwave Ichiro Hayakawa, Takuma Takemura, Emi Fukasawa, Yuta Ebihara, Natsuki Sato, Takayasu Nakamura, Kiyotake Suenaga, and Hideo Kigoshi Bull. Chem. Soc. Jpn. 2012, 85, 1077–1092. Open Access N O O O Conversion of Ethanol to Propene H Ph 10 mol% O Total Synthesis and Biological Evaluation of Auripyrones A and B H. Kigoshi D H Dynamic Kinetic Resolution Microwave 2.45 GHz Kazuya Nushiro, Satoshi Kikuchi, and Tohru Yamada Chem. Lett. 2013, 42, 165–167. Open Access BH doi: 10.1246/cl.2013.165 H3C Total Synthesis of Auripyrones A and B O Cl O tandem radical cyclization Editor’s Choice Extraordinary Microwave Effect on atropo-Enantioselective Catalytic Reduction of Biaryl Lactones T. Yamada A − 12 − doi: 10.1246/cl.2012.892 Triple-Ringed [14]Arene Open Access doi: 10.1246/cl.2012.699 Editor’s Choice Synthesis of Triple-ringed [14]Arene via Dynamic Covalent Chemistry Mechanism in Condensation Reaction of Phenols with m-Benzenedicarbaldehyde + & +2 2+ 2+ &+ &+ &+ 2+ +2 2+ +2 2+ +2 &+ 2+ H. Kudo Hiroyuki Seki, Shingo Kuwabara, Hiroto Kudo, and Tadatomi Nishikubo Chem. Lett. 2012, 41, 699–701. Peptide-Induced Nanoparticle Formation Open Access +2 + & 2+ +2 doi: 10.1246/bcsj.20120074 BCSJ Award Article Sn6O4(OH)4 30 min pH 6.2 Hisao Matsuno, Yuki Kawashima, and Takeshi Serizawa Bull. Chem. Soc. Jpn. 2012, 85, 746–752. Miniaturized Flow Reactors Open Access SnCl 2 pTO-7 peptide doi: 10.1246/cl.2012.562 FLOW REACTOR Ph NH 2 Andreas Kirschning, Lukas Kupracz, and Jan Hartwig Chem. Lett. 2012, 41, 562–570. Hydration of Nitriles nanoparticle based on Fe3O4/Fe2O3 Ph silica coating (70 %) doi: 10.1246/cl.2012.574 Letter R Kazuya Yamaguchi, Ye Wang, Hiroaki Kobayashi, and Noritaka Mizuno Chem. Lett. 2012, 41, 574–576. Directly Linked Corrole Oligomers N H [Pd(MeCN)4](BF4)2, FeCl3·6H2O (ClCH2)2/DMF (5:1) Efficient Hydration of Nitriles Promoted by Simple Amorphous Manganese Oxide Using Reduced Amounts of Water N. Mizuno 50 nm Highlight Review New Synthetic Opportunities in Miniaturized Flow Reactors with Inductive Heating A. Kirschning 2+ &+ 7ULSOHULQJHG>@DUHQH75$>@ Peptide-Induced Formation of Crystalline Sn6O4(OH)4 Nanoparticles under Ambient Conditions T. Serizawa 2+ +2 2+ +2 2+ +2 &+ &+ &+ Open Access BCSJ Award Article CN O H2O (2 equiv or less) amorphous MnO2 R NH2 doi: 10.1246/bcsj.20110373 Directly Linked Corrole Oligomers via Facile Oxidative 3–3′ Coupling Reaction N. Aratani Sho Hirabayashi, Masato Omote, Naoki Aratani, and Atsuhiro Osuka Bull. Chem. Soc. Jpn. 2012, 85, 558–562. − 13 − CSJ Journal Report Vol. 1 Phosphine Catalysis doi: 10.1246/cl.2012.218 Letter Phosphine-catalyzed [3 + 2] and [3 + 3] Annulations of Azomethine Imines with Ethyl 2-Butynoate H. Guo 2 1 1 Jun Liu, Honglei Liu, Risong Na, Guiyong Wang, Zhen Li, Hao Yu, Min Wang, Jiangchun Zhong, and Hongchao Guo Chem. Lett. 2012, 41, 218–220. Regioselective Hydrocarbamoylation Open Access Open Access &2(W &+&OUW 1 5 1 1 &2(W 5 1 &2(W doi: 10.1246/cl.2012.298 Editor’s Choice 2 1 Yosuke Miyazaki, Yuuya Yamada, Yoshiaki Nakao, and Tamejiro Hiyama Chem. Lett. 2012, 41, 298–300. One-Pot Synthesis of Furans 3%XPRO 5 Regioselective Hydrocarbamoylation of 1-Alkenes Y. Nakao 2 2 + 5 FDW1L,$G$O(W H[FOXVLYH OLQHDUVHOHFWLYLW\ 2 + 1 5 doi: 10.1246/bcsj.20110287 BCSJ Award Article One-Pot Synthesis of Furans from Various Saccharides Using a Combination of Solid Acid and Base Catalysts K. Ebitani β-Lactams Jaya Tuteja, Shun Nishimura, and Kohki Ebitani Bull. Chem. Soc. Jpn. 2012, 85, 275–281. doi: 10.1246/bcsj.20110323 Article Utilization of DMF–PhCOCl Adduct as an Acid Activator in a New and Convenient Method for Preparation of β-Lactams 1 2 3 R N=CHR + R CH2COOH M. Zarei DMF, PhCOCl Et3N, CH2Cl2, rt R2 R3 O N R1 Maaroof Zarei Bull. Chem. Soc. Jpn. 2012, 85, 360–368. Coupling Reactions of Aryl Halides Open Access Highlight Review Transition-metal-free Coupling Reactions of Aryl Halides E. Shirakawa Eiji Shirakawa and Tamio Hayashi Chem. Lett. 2012, 41, 130–134. CSJ Journal Report Vol. 1 − 14 − doi: 10.1246/cl.2012.130 One-Pot Sequential Reactions Open Access doi: 10.1246/cl.2012.2 Highlight Review Thioamides and Thioformamides for Sequential Reactions with Organolithium and Grignard Reagents S organolithium reagents Grignard reagents Toshiaki Murai and Yuichiro Mutoh Chem. Lett. 2012, 41, 2–8. MeS R − 15 − NR'2 OTf NR'2 SMe R R" R S R T. 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Highly-Correlated Electron Systems Open Access Award Accounts doi: 10.1246/bcsj.20130248 Electron-Transfer Processes in HighlyCorrelated Electron Systems of Thiazyl Radicals K. Awaga Kunio Awaga, Kenji Nomura, Hideo Kishida, Wataru Fujita, Hirofumi Yoshikawa, Michio M. Matsushita, Laigui Hu, Yoshiaki Shuku, and Rie Suizu Bull. Chem. Soc. Jpn. 2014, 87, 234–249. Zeolite-Templated Carbon Open Access doi: 10.1246/bcsj.20130292 BCSJ Award Article Large Pseudocapacitance in QuinoneFunctionalized Zeolite-Templated Carbon H. Nishihara Hiroyuki Itoi, Hirotomo Nishihara, Takafumi Ishii, Khanin Nueangnoraj, Raúl Berenguer-Betrián, and Takashi Kyotani Bull. Chem. Soc. Jpn. 2014, 87, 250–257. CSJ Journal Report Vol. 1 − 16 − Layer-by-Layer Nanoarchitectonics Open Access doi: 10.1246/cl.130987 Highlight Review Layer-by-layer Nanoarchitectonics: Invention, Innovation, and Evolution K. Ariga Katsuhiko Ariga, Yusuke Yamauchi, Gaulthier Rydzek, Qingmin Ji, Yusuke Yonamine, Kevin C.-W. 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Porous Coordination Frameworks Open Access Highlight Review doi: 10.1246/cl.130357 Control over Flexibility of Entangled Porous Coordination Frameworks by Molecular and Mesoscopic Chemistries S. Kitagawa Thin Films Shuhei Furukawa, Yoko Sakata, and Susumu Kitagawa Chem. Lett. 2013, 42, 570–576. Open Access doi: 10.1246/cl.130019 Editor’s Choice Substrate Dependence of the Proton Transport and Oriented Structure in Oligo[(1,2-propanediamine)-alt-(oxalic acid)] Thin Films Y. Nagao Yuki Nagao Chem. Lett. 2013, 42, 468–470. Thermoresponsive Chelating Polymer T. Saitoh Open Access BCSJ Award Article doi: 10.1246/bcsj.20120284 Preconcentration of Trace Metals in Water Using a Newly Designed Thermoresponsive Chelating Polymer for the Sensitive Determination by Graphite Furnace Atomic Absorption Spectrometry Tohru Saitoh, Akihiro Arakawa, and Masataka Hiraide Bull. Chem. Soc. Jpn. 2013, 86, 438–444. − 19 − CSJ Journal Report Vol. 1 Porous Coordination Polymer Open Access doi: 10.1246/cl.2013.222 Editor’s Choice Controlled Encapsulation of Photoresponsive Macromolecules in Porous Coordination Polymer T. Uemura Takashi Uemura, Gosuke Washino, Nobuhiro Yanai, and Susumu Kitagawa Chem. Lett. 2013, 42, 222–223. Transition-Metal Oxide Thin Films Open Access doi: 10.1246/bcsj.20120277 Award Accounts Reduction and Oxidation of TransitionMetal Oxide Thin Films: Solid-State Chemistry with Epitaxially Grown Thin Films Y. Shimakawa Yuichi Shimakawa Bull. Chem. Soc. Jpn. 2013, 86, 299–311. Magnetic Semiconductor Open Access doi: 10.1246/cl.2013.2 Highlight Review Magnetic Semiconductor EuO, EuS, and EuSe Nanocrystals for Future Optical Devices Y. Hasegawa Yasuchika Hasegawa Chem. Lett. 2013, 42, 2–7. Bimodal Magnetic Hydrogels Open Access Magnetoelastic Behavior of Bimodal Magnetic Hydrogels Using Nonmagnetic Particles T. 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DNA Origami Open Access doi: 10.1246/cl.2012.1459 Editor’s Choice Emergence of High-density DNA Origami Network by Dewetting with a Binary Solvent T. Matsumoto DNA origami in H2O Drying EtOH Yoshiaki Hirano, Kaoru Ojima, Yusuke Miyake, Tomoji Kawai, and Takuya Matsumoto Chem. Lett. 2012, 41, 1459–1461. π-Electron-System-Layered Polymers Open Access 2 µm 0.5 µm doi: 10.1246/cl.2012.840 Highlight Review π-Electron-system-layered Polymers Based on [2.2]Paracyclophane Y. Morisaki Yasuhiro Morisaki and Yoshiki Chujo Chem. Lett. 2012, 41, 840–846. Superhydrophobic Zinc Sulfide Films Open Access doi: 10.1246/cl.2012.915 Editor’s Choice In Situ Fabrication of Superhydrophobic Zinc Sulfide Films on a Flexible Zinc Foil Substrate Y. Zhang Yidong Zhang and Liwei Mi Chem. Lett. 2012, 41, 915–916. Novel π-Conjugated Systems T. 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Shimoda Zhongrong Shen, Yasuo Matsuki, Koichi Higashimine, Mikio Miyake, and Tatsuya Shimoda Chem. Lett. 2012, 41, 644–646. Colloid and Interface under Magnetic Fields Open Access Highlight Review doi: 10.1246/cl.2012.342 Colloid and Interface Chemistry under Magnetic Fields S. Ozeki Ayumi Sakaguchi, Atom Hamasaki, and Sumio Ozeki Chem. Lett. 2012, 41, 342–348. Highly Luminescent Nanoparticles doi: 10.1246/cl.2012.397 Letter Highly Luminescent Lead Bromide Perovskite Nanoparticles Synthesized with Porous Alumina Media A. Kojima ([FLWDWLRQ OLJKW /HDGEURPLGHSHURYVNLWH QDQRSDUWLFOH Akihiro Kojima, Masashi Ikegami, Kenjiro Teshima, and Tsutomu Miyasaka Chem. Lett. 2012, 41, 397–399. Hierarchical Cell Manipulation Open Access 0HVRSRURXV$O2 ILOP Award Accounts Development of Three-Dimensional Tissue Models Based on Hierarchical Cell Manipulation Using Nanofilms M. Matsusaki Michiya Matsusaki Bull. Chem. Soc. Jpn. 2012, 85, 401–414. CSJ Journal Report Vol. 1 *UHHQFRORU SKRWROXPLQHVFHQFH − 22 − doi: 10.1246/bcsj.20110194 Coordination Networks Open Access doi: 10.1246/bcsj.20110361 BCSJ Award Article Hetero Bi-Paddle-Wheel Coordination Networks: A New Synthetic Route to Rh-Containing Metal–Organic Frameworks Rh2 paddle-wheel unit S. Matsunaga Satoshi Matsunaga, Ken-ichi Hasada, Kenji Sugiura, Naoki Kitamura, Yuri Kudo, Nanako Endo, and Wasuke Mori Bull. Chem. Soc. Jpn. 2012, 85, 433–438. Trimethylsumanene Cu2 or Zn2 paddle-wheel unit doi: 10.1246/bcsj.20110286 Selected Paper Trimethylsumanene: Enantioselective Synthesis, Substituent Effect on Bowl Structure, Inversion Energy, and Electron Conductivity H. Sakurai Shuhei Higashibayashi, Ryoji Tsuruoka, Yarasi Soujanya, Uppula Purushotham, G. Narahari Sastry, Shu Seki, Takeharu Ishikawa, Shinji Toyota, and Hidehiro Sakurai Bull. Chem. Soc. Jpn. 2012, 85, 450–467. Self-Assembled Nanogel Open Access doi: 10.1246/cl.2012.202 Highlight Review Self-assembled Nanogel Engineering for Advanced Biomedical Technology K. Akiyoshi Yoshihiro Sasaki and Kazunari Akiyoshi Chem. Lett. 2012, 41, 202–208. Polymer Particles Open Access doi: 10.1246/bcsj.20110197 Award Accounts Creation of Functional and Structured Polymer Particles by Self-Organized Precipitation (SORP) H. Yabu Hiroshi Yabu Bull. Chem. Soc. Jpn. 2012, 85, 265–274. Molecular Conductor Open Access doi: 10.1246/cl.2012.154 Editor’s Choice Single-component Layered Molecular Conductor, [Au(ptdt)2] A. Kobayashi Biao Zhou, Hiroyuki Yajima, Yuki Idobata, Akiko Kobayashi, Tetsuya Kobayashi, Eiji Nishibori, Hiroshi Sawa, and Hayao Kobayashi Chem. 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Non-Siliceous Porous Materials Open Access C16 doi: 10.1246/bcsj.20110279 Award Accounts Development of Non-Siliceous Porous Materials and Emerging Applications K. Fujita Koji Fujita Bull. Chem. Soc. Jpn. 2012, 85, 415–432. Nanoarchitectonics for Mesoporous Materials Open Access Accounts Thomson Reuters Research Fronts doi: 10.1246/bcsj.20110162 Nanoarchitectonics for Mesoporous Materials K. Ariga Katsuhiko Ariga, Ajayan Vinu, Yusuke Yamauchi, Qingmin Ji, and Jonathan P. Hill Bull. Chem. Soc. Jpn. 2012, 85, 1–32. − 25 − CSJ Journal Report Vol. 1 Metal Catalysis Hydrodesulfurization (HDS) Catalysts Y. Okamoto Open Access doi: 10.1246/bcsj.20130204 Accounts Novel Molecular Approaches to the Structure–Activity Relationships and Unique Characterizations of Co–Mo Sulfide Hydrodesulfurization Catalysts for the Production of Ultraclean Fuels CoMoS MoS 2 support Mo2S4 CVDCoMo Co 2Mo 2S6 Production of Cleaner Fuels Yasuaki Okamoto Bull. Chem. Soc. Jpn. 2014, 87, 20–58. Si–CN Bond Cleavage Open Access doi: 10.1246/bcsj.20130206 BCSJ Award Article Si–CN Bond Cleavage of Silyl Cyanides by an Iron Catalyst. A New Route of Silyl Cyanide Formation H. Nakazawa cat. Andrea Renzetti, Nobuaki Koga, and Hiroshi Nakazawa Bull. Chem. Soc. Jpn. 2014, 87, 59–68. Cu-Catalyzed Aerobic Molecular Transformation R 3SiCN + R' 3SiH Open Access R 3SiH + R' 3SiCN doi: 10.1246/bcsj.20130220 R' R" Ph Ph CN N2 NH CN N R2 N + R-MgBr Ph NH CO2 Et Ph Me NH Ph + R-MgBr R1 NH O Ph Powered by Cu-Catalyzed Aerobic Reactions R2 N Shunsuke Chiba Bull. Chem. Soc. Jpn. 2013, 86, 1400–1411. NH "[Cu] + O2" O S. Chiba Open Access Me Award Accounts Cu-Catalyzed Aerobic Molecular Transformation of Imine and Enamine Derivatives for Synthesis of Azaheterocycles Gold Catalysis Fe OC C O O R' N R1 R N N N N R R" R' O Ph O R O HN H CO2Et Ph Ph H CO2 Et NH2 Ph N Ph Ph O Me N Ph N doi: 10.1246/bcsj.20130075 BCSJ Award Article Aerobic Oxidation of Sulfides to Sulfoxides Catalyzed by Gold/Manganese Oxides M. Haruta Ayako Taketoshi, Patricia Concepción, Hermenegildo García, Avelino Corma, and Masatake Haruta Bull. Chem. Soc. Jpn. 2013, 86, 1412–1418. Functionalization of Aromatic Rings Open Access Direct Functionalization of Aromatic Rings on Platinum-loaded Titanium Oxide Photocatalyst H. Yoshida X X H2O Photocatalysis by Pt/TiO 2 Hayato Yuzawa and Hisao Yoshida Chem. Lett. 2013, 42, 1336–1343. CSJ Journal Report Vol. 1 doi: 10.1246/cl.130757 Highlight Review NH3(aq) − 26 − OH + H2 X Hydroxylation NH2 + H2 Amination Hydrogenation of Nitroaromatics Open Access doi: 10.1246/cl.130333 Editor’s Choice Selective Hydrogenation of Nitroaromatics by Colloidal Iridium Nanoparticles T. Tsukuda Md. J. Sharif, Prasenjit Maity, Seiji Yamazoe, and Tatsuya Tsukuda Chem. Lett. 2013, 42, 1023–1025. C–H Activation Open Access doi: 10.1246/cl.130228 Editor’s Choice Synthesis of Spirooxindoles from Carbamoyl Chlorides via Cyclopropyl Methine C(sp3)–H Activation Using Palladium Catalyst R1 N C. Tsukano Open Access doi: 10.1246/bcsj.20130004 R or Naohiro Kirai, Shoichiro Iguchi, Tatsuyoshi Ito, Jun Takaya, and Nobuharu Iwasawa Bull. Chem. Soc. Jpn. 2013, 86, 784–799. Chemoselective Reduction of Unsaturated Aldehydes B2pin2 cat. AlEt 3 cat. (PSiP )PdOTf R R Bpin Bpin Ar2P Pd Bpin R Bpin R' R' R Bpin Bpin Bpin PAr 2 Si Bpin Bpin R R R' K. Kaneda O R1 Cs2CO3 (1.1 equiv) N pivNHOH (30 mol%) CO (1 atm), mesitylene R2 40-85% 120 °C (11 examples) BCSJ Award Article PSiP-Pincer Type Palladium-Catalyzed Dehydrogenative Borylation of Alkenes and 1,3-Dienes N. Iwasawa Cl R2 Chihiro Tsukano, Masataka Okuno, and Yoshiji Takemoto Chem. Lett. 2013, 42, 753–755. PSiP-Pincer Type Palladium Catalyst Pd(OAc)2 (3 mol%) Ad2Pn Bu (6 mol%) O (with 1 equiv B2pin2) (with 2 equiv B2pin2) Me Active species Open Access doi: 10.1246/cl.130132 Editor’s Choice Remarkable Effect of Bases on Core–Shell AgNP@CeO2 Nanocomposite-catalyzed Highly Chemoselective Reduction of Unsaturated Aldehydes Takato Mitsudome, Motoshi Matoba, Masaaki Yamamoto, Tomoo Mizugaki, Koichiro Jitsukawa, and Kiyotomi Kaneda Chem. Lett. 2013, 42, 660–662. doi: 10.1246/cl.121287 Editor’s Choice Effects of Copper(II) Oxide Addition and Red Light Irradiation on Photocatalytic Activity of Indium Oxide under Irradiation of Visible Light H. Kominami Yasutomo Sasaki, Atsuhiro Tanaka, Keiji Hashimoto, and Hiroshi Kominami Chem. Lett. 2013, 42, 419–421. ,Q2 &X2,Q2 ZLWKRXW UHGOLJKW − 27 − &X2,Q2 ZLWKUHGOLJKW :DYHOHQJWKQP $4( Open Access >UHIOHFWLRQ@ Photocatalysts CSJ Journal Report Vol. 1 High-Molecular-Weight Polymer A. Mori Open Access doi: 10.1246/cl.2013.281 Editor’s Choice Synthesis of High-molecular-weight Head-to-tail-type Poly(3-substitutedthiophene)s by Cross-coupling Polycondensation with [CpNiCl(NHC)] as a Catalyst i i n Coupling Reactions Open Access H S Hex Pr Self-standing P3HT film Ni n n 74%, M w =815000 M w /M n=3.49 doi: 10.1246/cl.2013.94 R3 R4 R2 R4 X R3 R1 H NHC-Metal complex R2 + Miguel Yus and Isidro M. Pastor Chem. Lett. 2013, 42, 94–108. Open Access Hex [CpNiCl(SIPr)] Highlight Review R2 or R2 H R1 doi: 10.1246/cl.2012.1554 Highlight Review Cu–Rh Redox Relay Catalysts for Synthesis of Azaheterocycles via C–H Functionalization S. Chiba i Pr Pr S R1 C–H Functionalization N Br Heterocyclic Carbene–Metal-catalyzed Csp2–Csp2 and Csp–Csp2 Couplings Using Nonmetallic Substrates M. Yus i N Cl TMPMgCl·LiCl Shunsuke Tamba, Kanta Fuji, Hikaru Meguro, Shuji Okamoto, Tadashi Tendo, Ryo Komobuchi, Atsushi Sugie, Takashi Nishino, and Atsunori Mori Chem. Lett. 2013, 42, 281–283. Pr N2 H R' N + R R' N DMF, 90 °C R" Vinyl Azides R" cat. [Cp*RhCl2]2 cat. Cu(OAc)2 AcOH R Rh(III) process II oxidation 2 Cu(I) process I reduction 2 Cu(II) Rh(I) Cu-Rh relay catalysts Shunsuke Chiba Chem. Lett. 2012, 41, 1554–1559. OAc H R' N R + R" cat. [Cp*RhCl2]2 cat. Cu(OAc)2 R' N R DMF, 60 °C R" Oximes syn -anti mixtures Transformations of Nitriles and Amides Open Access doi: 10.1246/cl.2012.1397 Highlight Review CeO2-catalyzed Transformations of Nitriles and Amides K. Shimizu One-pot esterification O 1 R Masazumi Tamura, Ken-ichi Shimizu, and Atsushi Satsuma Chem. Lett. 2012, 41, 1397–1405. 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