Cyanotrifluoromethylthiolation of unactivated dialkyl-substituted alkynes via cyano migration: synthesis of trifluoromethylthiolated acrylonitriles

Herein a novel, elusive cyanotrifluoromethylthiolation of unactivated dialkyl-substituted alkynes is reported. Taking advantage of the intramolecular cyano migration strategy, the reaction proceeds stereoselectively to deliver E-olefinic products. A variety of tetrasubstituted trifluoromethylthiolat...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2018, Vol.54 (50), p.6812-6815
Main Authors: Ji, Meishan, Yu, Jiajia, Zhu, Chen
Format: Article
Language:English
Subjects:
Acrylonitriles
Alkynes
Migration
Substitutes
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Summary:Herein a novel, elusive cyanotrifluoromethylthiolation of unactivated dialkyl-substituted alkynes is reported. Taking advantage of the intramolecular cyano migration strategy, the reaction proceeds stereoselectively to deliver E-olefinic products. A variety of tetrasubstituted trifluoromethylthiolated acrylonitriles are afforded in modest to good yields.
ISSN:1359-7345
1364-548X
DOI:10.1039/c8cc01189c