Issue 41, 2023

Directing group assisted para-selective C–H alkynylation of unbiased arenes enabled by rhodium catalysis

Abstract

Regioselective C–H alkynylation of arenes via C–H activation is challenging yet a highly desirable transformation. In this regard, directing group assisted C(sp2)–H alkynylation of arenes offers a unique opportunity to ensure precise regioselectivity. While the existing methods are mainly centered around ortho-C–H alkynylation and a few for meta-C–H alkynylation, the DG-assisted para-selective C–H alkynylation is yet to be reported. Herein we disclose the first report on Rh-catalyzed para-C–H alkynylation of sterically and electronically unbiased arenes. The para-selectivity is achieved with the assistance of a cyano-based directing template and the selectivity remained unaltered irrespective of the steric and electronic influence of the substituents. The post-synthetic modification of synthesized para-alkynylated arenes is also demonstrated. The mechanistic intricacies of the developed protocol are elucidated through experimental and computational studies.

Graphical abstract: Directing group assisted para-selective C–H alkynylation of unbiased arenes enabled by rhodium catalysis

Supplementary files

Article information

Article type
Edge Article
Submitted
10 jul. 2023
Accepted
18 sep. 2023
First published
20 sep. 2023
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., 2023,14, 11381-11388

Directing group assisted para-selective C–H alkynylation of unbiased arenes enabled by rhodium catalysis

U. Dutta, G. Prakash, K. Devi, K. Borah, X. Zhang and D. Maiti, Chem. Sci., 2023, 14, 11381 DOI: 10.1039/D3SC03528J

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