Issue 4, 2024

A gold-catalyzed cyclization/nucleophilic addition reaction of o-alkynylanilines with ynamides: stereoselective synthesis of 3-vinylindoles

Abstract

Functionalized 3-vinylindoles were obtained through the cyclization/nucleophilic addition of ynamides and o-alkynylanilines catalyzed by a gold catalyst with high stereoselectivity and site-selectivity. The theoretical research suggested that the Cα of ynamides activated by the gold complex was favorable for the addition at the C3 position of indoles. Additionally, JohnPhosAu(MeCN)SbF6 could efficiently reduce the activation energy barrier of the addition process compared to PicAuCl2 and Au(PPh3)NTf2, and the steric hindrance effect of JohnPhosAu(MeCN)SbF6 facilitates the formation of 3-vinylindoles with the E configuration.

Graphical abstract: A gold-catalyzed cyclization/nucleophilic addition reaction of o-alkynylanilines with ynamides: stereoselective synthesis of 3-vinylindoles

Supplementary files

Article information

Article type
Research Article
Submitted
23 Oct 2023
Accepted
19 Dec 2023
First published
23 Dec 2023

Org. Chem. Front., 2024,11, 1112-1117

A gold-catalyzed cyclization/nucleophilic addition reaction of o-alkynylanilines with ynamides: stereoselective synthesis of 3-vinylindoles

W. Luo, Q. Chen, X. Mo, J. Jiang and P. Xie, Org. Chem. Front., 2024, 11, 1112 DOI: 10.1039/D3QO01753B

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