Yb()-catalysed -thioallylation of ynamides

• Published in: Chemical communications (Cambridge, England) England), 2021-07, Vol.57 (61), p.7521-7524
• Main Authors: Gogoi, Manash Protim, Vanjari, Rajeshwer, Prabagar, B, Yang, Shengwen, Dutta, Shubham, Mallick, Rajendra K, Gandon, Vincent, Sahoo, Akhila K
• Format: Article
• ISSN: 1359-7345; 1364-548X
• DOI: 10.1039/d1cc02611a

Reported herein is a syn -thioallylation of ynamides incorporating a sulfide moiety at the α-position and an allyl group at the β-position of the ynamide. The transformation is successful under ytterbium( iii )-catalysis, providing access to highly substituted thioamino-skipped-dienes with broad substrate scope. Thus, tetrasubstituted olefins (with four different functional groups: amide, phenyl, thioaryl/alkyl, and allyl on the carbon centers) are made in a single step from readily accessible ynamides, preserving complete atom economy. The reaction can be extended to the synthesis of selenoamino dienes by ynamide syn -selenoallylation. DFT studies and control experiments provide insight into the reaction mechanism. Reported herein is a syn -thioallylation of ynamides incorporating a sulfide moiety at the α-position and an allyl group at the β-position of the ynamide.