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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.
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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
Affiliated Colleges: