Yb(iii)-catalysed syn-thioallylation of ynamides

Gogoi, Manash Protim ; Vanjari, Rajeshwer ; Prabagar, B. ; Yang, Shengwen ; Dutta, Shubham ; Mallick, Rajendra K. ; Gandon, Vincent ; Sahoo, Akhila K. (2021) Yb(iii)-catalysed syn-thioallylation of ynamides Chemical Communications, 57 (61). pp. 7521-7524. ISSN 1359-7345

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Official URL: http://doi.org/10.1039/D1CC02611A

Related URL: http://dx.doi.org/10.1039/D1CC02611A

Abstract

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.

Item Type:Article
Source:Copyright of this article belongs to Royal Society of Chemistry.
ID Code:122474
Deposited On:02 Aug 2021 19:24
Last Modified:02 Aug 2021 19:24

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