Issue 34, 2022

Palladium-catalyzed nucleomethylation of alkynes for synthesis of methylated heteroaromatic compounds

Abstract

Herein, we disclosed a novel and efficient palladium-catalyzed nucleomethylation of alkynes for the simultaneous construction of the heteroaromatic ring and methyl group. The 3-methylindoles, 3-methylbenzofurans and 4-methylisoquinolines were obtained in moderate to excellent yields. Notably, this methodology was employed as a key step for synthesis of a pregnane X receptor antagonist, zindoxifene, bazedoxifene and AFN-1252. The kinetic studies revealed that reductive elimination might be the rate-determining step.

Graphical abstract: Palladium-catalyzed nucleomethylation of alkynes for synthesis of methylated heteroaromatic compounds

Supplementary files

Article information

Article type
Edge Article
Submitted
13 Jun 2022
Accepted
09 Aug 2022
First published
18 Aug 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2022,13, 10095-10102

Palladium-catalyzed nucleomethylation of alkynes for synthesis of methylated heteroaromatic compounds

X. Yang, G. Wang and Z. Ye, Chem. Sci., 2022, 13, 10095 DOI: 10.1039/D2SC03294E

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