Copper-Catalyzed Regioselective Aminothiolation of Aromatic and Aliphatic Alkenes with N-Fluorobenzenesulfonimide and Thiols through Three-Component Radical Coupling

Masayuki Iwasaki; Kosei Nonaka; Song Zou; Yuta Sawanaka; Takaaki Shinozaki; Tomoya Fujii; Kiyohiko Nakajima; Yasushi Nishihara

doi:10.1021/acs.joc.9b02392

Copper-Catalyzed Regioselective Aminothiolation of Aromatic and Aliphatic Alkenes with N-Fluorobenzenesulfonimide and Thiols through Three-Component Radical Coupling

Masayuki Iwasaki, Kosei Nonaka, Song Zou, Yuta Sawanaka, Takaaki Shinozaki, Tomoya Fujii, Kiyohiko Nakajima, Yasushi Nishihara

Research Institute for Interdisciplinary Science

Research output: Contribution to journal › Article › peer-review

2 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	15373-15379
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	84
Issue number	23
DOIs	https://doi.org/10.1021/acs.joc.9b02392
Publication status	Published - Dec 6 2019

ASJC Scopus subject areas

Organic Chemistry

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Copper-Catalyzed Regioselective Aminothiolation of Aromatic and Aliphatic Alkenes with N-Fluorobenzenesulfonimide and Thiols through Three-Component Radical Coupling. / Iwasaki, Masayuki; Nonaka, Kosei; Zou, Song; Sawanaka, Yuta; Shinozaki, Takaaki; Fujii, Tomoya; Nakajima, Kiyohiko; Nishihara, Yasushi.

In: Journal of Organic Chemistry, Vol. 84, No. 23, 06.12.2019, p. 15373-15379.

Research output: Contribution to journal › Article › peer-review

Iwasaki, M, Nonaka, K, Zou, S, Sawanaka, Y, Shinozaki, T, Fujii, T, Nakajima, K & Nishihara, Y 2019, 'Copper-Catalyzed Regioselective Aminothiolation of Aromatic and Aliphatic Alkenes with N-Fluorobenzenesulfonimide and Thiols through Three-Component Radical Coupling', Journal of Organic Chemistry, vol. 84, no. 23, pp. 15373-15379. https://doi.org/10.1021/acs.joc.9b02392

Iwasaki, Masayuki ; Nonaka, Kosei ; Zou, Song ; Sawanaka, Yuta ; Shinozaki, Takaaki ; Fujii, Tomoya ; Nakajima, Kiyohiko ; Nishihara, Yasushi. / Copper-Catalyzed Regioselective Aminothiolation of Aromatic and Aliphatic Alkenes with N-Fluorobenzenesulfonimide and Thiols through Three-Component Radical Coupling. In: Journal of Organic Chemistry. 2019 ; Vol. 84, No. 23. pp. 15373-15379.

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abstract = "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.",

author = "Masayuki Iwasaki and Kosei Nonaka and Song Zou and Yuta Sawanaka and Takaaki Shinozaki and Tomoya Fujii and Kiyohiko Nakajima and Yasushi Nishihara",

note = "Funding Information: This work was partly supported by Grant-in-Aid for Scientific Research (KAKENHI) (no. 16K17901) from JSPS. The authors gratefully thank Megumi Kosaka and Motonari Kobayashi (Department of Instrumental Analysis, Advanced Science Research Center, Okayama University) for performing elemental analyses, and the SC-NMR Laboratory (Okayama University) for the NMR spectral measurements. ",

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AU - Nonaka, Kosei

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AU - Sawanaka, Yuta

AU - Shinozaki, Takaaki

AU - Fujii, Tomoya

AU - Nakajima, Kiyohiko

AU - Nishihara, Yasushi

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PY - 2019/12/6

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