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author:

Rong, Mingguang (Rong, Mingguang.) [1] | Li, Dongzhe (Li, Dongzhe.) [2] | Huang, Ronglu (Huang, Ronglu.) [3] | Huang, Yangjie (Huang, Yangjie.) [4] | Han, Xiaoyan (Han, Xiaoyan.) [5] | Weng, Zhiqiang (Weng, Zhiqiang.) [6]

Indexed by:

Scopus SCIE

Abstract:

An efficient method is reported for the copper(I)-catalyzed trifluoromethylthiolation of allylic bromides by using elemental sulfur and CF3SiMe3. This rate of this transformation was significantly accelerated in the presence of 18-crown-6, and the reaction afforded the desired products in moderate to excellent yields with high stereo- and regioselectivity. This method can tolerate a number of functional groups and provides facile access to a variety of allylic trifluoromethyl thioethers. The copper(I)-catalyzed trifluoromethylthiolation of propargylic chlorides was also investigated. A plausible mechanism that involves an allylcopper(III) intermediate is proposed.

Keyword:

Alkynes Allylic compounds Fluorine Regioselectivity Sulfur Synthetic methods

Community:

  • [ 1 ] [Rong, Mingguang]Fuzhou Univ, Dept Chem, Fuzhou 350108, Peoples R China
  • [ 2 ] [Li, Dongzhe]Fuzhou Univ, Dept Chem, Fuzhou 350108, Peoples R China
  • [ 3 ] [Huang, Ronglu]Fuzhou Univ, Dept Chem, Fuzhou 350108, Peoples R China
  • [ 4 ] [Huang, Yangjie]Fuzhou Univ, Dept Chem, Fuzhou 350108, Peoples R China
  • [ 5 ] [Weng, Zhiqiang]Fuzhou Univ, Dept Chem, Fuzhou 350108, Peoples R China
  • [ 6 ] [Han, Xiaoyan]Soochow Univ, Testing & Anal Ctr, Suzhou 215123, Peoples R China

Reprint 's Address:

  • [Han, Xiaoyan]Soochow Univ, Testing & Anal Ctr, Suzhou 215123, Peoples R China

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Source :

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

ISSN: 1434-193X

Year: 2014

Issue: 23

Volume: 2014

Page: 5010-5016

3 . 0 6 5

JCR@2014

2 . 5 0 0

JCR@2023

ESI Discipline: CHEMISTRY;

ESI HC Threshold:268

JCR Journal Grade:1

CAS Journal Grade:3

Cited Count:

WoS CC Cited Count: 22

SCOPUS Cited Count: 23

ESI Highly Cited Papers on the List: 0 Unfold All

WanFang Cited Count:

Chinese Cited Count:

30 Days PV: 0

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