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 output: Contribution to journalArticle

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 languageEnglish
JournalJournal of Organic Chemistry
DOIs
Publication statusAccepted/In press - Jan 1 2019

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Alkenes
Sulfhydryl Compounds
Copper
Clocks
N-fluorobenzenesulfonimide
Experiments

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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, 01.01.2019.

Research output: Contribution to journalArticle

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AU - Nonaka, Kosei

AU - Zou, Song

AU - Sawanaka, Yuta

AU - Shinozaki, Takaaki

AU - Fujii, Tomoya

AU - Nakajima, Kiyohiko

AU - Nishihara, Yasushi

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