TY - JOUR
T1 - Copper-Catalyzed Regioselective Aminothiolation of Aromatic and Aliphatic Alkenes with N-Fluorobenzenesulfonimide and Thiols through Three-Component Radical Coupling
AU - Iwasaki, Masayuki
AU - Nonaka, Kosei
AU - Zou, Song
AU - Sawanaka, Yuta
AU - Shinozaki, Takaaki
AU - Fujii, Tomoya
AU - Nakajima, Kiyohiko
AU - Nishihara, Yasushi
N1 - 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.
Publisher Copyright:
© 2019 American Chemical Society.
PY - 2019/12/6
Y1 - 2019/12/6
N2 - 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.
AB - 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.
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U2 - 10.1021/acs.joc.9b02392
DO - 10.1021/acs.joc.9b02392
M3 - Article
C2 - 31696696
AN - SCOPUS:85075423238
VL - 84
SP - 15373
EP - 15379
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 23
ER -