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author:

Rong, M. (Rong, M..) [1] | Li, D. (Li, D..) [2] | Huang, R. (Huang, R..) [3] | Huang, Y. (Huang, Y..) [4] | Han, X. (Han, X..) [5] | Weng, Z. (Weng, Z..) [6]

Indexed by:

Scopus

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. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keyword:

Alkynes; Allylic compounds; Fluorine; Regioselectivity; Sulfur; Synthetic methods

Community:

  • [ 1 ] [Rong, M.]Department of Chemistry, Fuzhou University, Fuzhou 350108, China
  • [ 2 ] [Li, D.]Department of Chemistry, Fuzhou University, Fuzhou 350108, China
  • [ 3 ] [Huang, R.]Department of Chemistry, Fuzhou University, Fuzhou 350108, China
  • [ 4 ] [Huang, Y.]Department of Chemistry, Fuzhou University, Fuzhou 350108, China
  • [ 5 ] [Han, X.]Testing and Analysis Center, Soochow University, Suzhou 215123, China
  • [ 6 ] [Weng, Z.]Department of Chemistry, Fuzhou University, Fuzhou 350108, China

Reprint 's Address:

  • [Han, X.]Testing and Analysis Center, Soochow University, Suzhou 215123, 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 HC Threshold:268

JCR Journal Grade:1

CAS Journal Grade:3

Cited Count:

WoS CC Cited Count:

SCOPUS Cited Count: 23

ESI Highly Cited Papers on the List: 0 Unfold All

WanFang Cited Count:

Chinese Cited Count:

30 Days PV: 1

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