Issue 20, 2024

Me3SiBr-promoted cascade electrophilic thiocyanation/cyclization of ortho-alkynylanilines to synthesize indole derivatives

Abstract

A Lewis acid-promoted electrophilic thiocyanation/cyclization of ortho-alkynylanilines for the synthesis of indole derivatives has been developed. The reaction utilizes Me3SiBr as the Lewis acid and N-thiocyanatosuccinimide as the thiocyanation reagent. A series of 2-aryl-3-thiocyanato indoles were prepared in moderate to high yields under mild conditions without metals and oxidants. It provides an efficient protocol for the construction of the indole skeleton and C–SCN and C–N bonds in one step as well.

Graphical abstract: Me3SiBr-promoted cascade electrophilic thiocyanation/cyclization of ortho-alkynylanilines to synthesize indole derivatives

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Article information

Article type
Communication
Submitted
06 Mar 2024
Accepted
24 Apr 2024
First published
25 Apr 2024

Org. Biomol. Chem., 2024,22, 4031-4035

Me3SiBr-promoted cascade electrophilic thiocyanation/cyclization of ortho-alkynylanilines to synthesize indole derivatives

Q. Wang, C. Shao, R. Hua, H. Yin and F. Chen, Org. Biomol. Chem., 2024, 22, 4031 DOI: 10.1039/D4OB00367E

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