American Chemical Society Acta Medica Okayama 0022-3263 84 23 2019 Copper-Catalyzed Regioselective Aminothiolation of Aromatic and Aliphatic Alkenes with N-Fluorobenzenesulfonimide and Thiols through Three-Component Radical Coupling 15373 15379 EN Masayuki Iwasaki Research Institute for Interdisciplinary Science, Okayama University Kosei Nonaka Graduate School of Natural Science and Technology, Okayama University Song Zou Yuta Sawanaka Graduate School of Natural Science and Technology, Okayama University Takaaki Shinozaki Graduate School of Natural Science and Technology, Okayama University Tomoya Fujii Graduate School of Natural Science and Technology, Okayama University Kiyohiko Nakajima Graduate School of Natural Science and Technology, Okayama University Yasushi Nishihara Research Institute for Interdisciplinary Science, Okayama University Copper-catalyzed regioselective aminothiolation of terminal and internal alkenes with N-fluorobenzenesulfonimide and thiols has been developed. The three-component reaction is promoted by the addition of dimethyl sulfide. In addition to aromatic alkenes, aliphatic alkenes are subjected to the reaction, affording various aminothiolation adducts as single regioisomers. The radical process is proposed by preliminary mechanistic studies, involving radical trap and radical clock experiments. No potential conflict of interest relevant to this article was reported.

Chemical Society of Japan Acta Medica Okayama 03667022 48 3 2019 Copper-catalyzed Regioselective Chloroamination of Alkenes with Chlorotrimethylsilane and N-Fluorobenzenesulfonimide under Microwave-assisted Conditions 281 283 EN Masayuki Iwasaki Research Institute for Interdisciplinary Science, Okayama University Jie Xu Graduate School of Natural Science and Technology, Okayama University Yukari Tani Graduate School of Natural Science and Technology, Okayama University Liyan Fu Graduate School of Natural Science and Technology, Okayama University Yuichi Ikemoto Graduate School of Natural Science and Technology, Okayama University Yasuyuki Ura Department of Chemistry, Biology, and Environmental Science, Faculty of Science, Nara Women’s University Yasushi Nishihara Research Institute for Interdisciplinary Science, Okayama University A copper-catalyzed chloroamination of alkenes with chlorotrimethylsilane and N-fluorobenzenesulfonimide has been developed. The reactions were complete within 1 h at 120 degrees C by means of microwave heating. The present chloroamination proceeds with a perfect regioselectivity and is compatible with various functional groups. The preliminary mechanistic investigation revealed that the reaction involves a radical process. The utility of the present method was demonstrated by scalable, operationally simple and safe system. No potential conflict of interest relevant to this article was reported.

American Chemical Society Acta Medica Okayama 1523-7060 18 7 2016 Palladium-Catalyzed Regio- and Stereoselective Carbothiolation of Terminal Alkynes with Azolyl Sulfides 1642 1645 EN Masayuki Iwasaki Division of Earth, Life, and Molecular Sciences, Graduate School of Natural Science and Technology, Okayama University Nikola Topolovčan Division of Earth, Life, and Molecular Sciences, Graduate School of Natural Science and Technology, Okayama University Hao Hu Division of Earth, Life, and Molecular Sciences, Graduate School of Natural Science and Technology, Okayama University Yugo Nishimura Division of Earth, Life, and Molecular Sciences, Graduate School of Natural Science and Technology, Okayama University Glwadys Gagnot Division of Earth, Life, and Molecular Sciences, Graduate School of Natural Science and Technology, Okayama University Rungsaeng Na nakorn Division of Earth, Life, and Molecular Sciences, Graduate School of Natural Science and Technology, Okayama University Ramida Yuvacharaskul Division of Earth, Life, and Molecular Sciences, Graduate School of Natural Science and Technology, Okayama University Kiyohiko Nakajima Department of Chemistry, Aichi University of Education Yasushi Nishihara Division of Earth, Life, and Molecular Sciences, Graduate School of Natural Science and Technology, Okayama University Palladium-catalyzed carbothiolation of terminal alkynes with azolyl sulfides affords various 2-(azolyl)alkenyl sulfides with perfect regio- and stereoselectivities. The present addition reaction proceeded through a direct cleavage of carbon-sulfur bonds in azolyl sulfides. The resulting adducts that are useful intermediates in organic synthesis are further transformed to multisubstituted olefins containing azolyl moieties. No potential conflict of interest relevant to this article was reported.

American Chemical Society Acta Medica Okayama 1523-7060 19 5 2017 Synthesis of Benzoisoselenazolone Derivatives by Nickel-Catalyzed Dehydrogenative Direct Selenation of C(sp2)-H Bonds with Elemental Selenium in Air 1092 1095 EN Masayuki Iwasaki Research Institute for Interdisciplinary Science, Okayama University Natsumi Miki Graduate School of Natural Science and Technology, Okayama University Yuta Tsuchiya Graduate School of Natural Science and Technology, Okayama University Kiyohiko Nakajima Department of Chemistry, Aichi University of Education Yasushi Nishihara Research Institute for Interdisciplinary Science, Okayama University Nickel-catalyzed direct selenation of benzamides bearing an 8-quinolyl auxiliary with elemental selenium provides benzoisoselenazolones in good yield via carbon-selenium and nitrogen-selenium bond formation under aerobic conditions. In addition to aryl C-H bonds, the method can also be applied to alkenyl C-H bonds, constructing an isoselenazolone skeleton. Simple mechanistic analysis shows that the reaction proceeds through a rate-determining C-H bond cleavage. The obtained benzoisoselenazolones are transformed into various organoselenium compounds and utilized as the catalyst for bromolactonization of alkenoic acids. No potential conflict of interest relevant to this article was reported.