Directing Group Assisted Rhodium Catalyzed -C-H Alkynylation of Arenes

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2022 Jun 13

PMID 35694332

Authors

Sheuli Sasmal

Gaurav Prakash

Uttam Dutta

Ranjini Laskar

Goutam Kumar Lahiri

Debabrata Maiti

Affiliations

Soon will be listed here.

Abstract

Site-selective C-H alkynylation of arenes to produce aryl alkynes is a highly desirable transformation due to the prevalence of aryl alkynes in various natural products, drug molecules and in materials. To ensure site-selective C-H functionalization, directing group (DG) assisted C-H activation has been evolved as a useful synthetic tool. In contrast to DG-assisted -C-H activation, distal -C-H activation is highly challenging and has attracted significant attention in recent years. However, developments are majorly focused on Pd-based catalytic systems. In order to diversify the scope of distal -C-H functionalization, herein we disclosed the first Rh(i) catalyzed -C-H alkynylation protocol through the inverse Sonogashira coupling reaction. The protocol is compatible with various substrate classes which include phenylacetic acids, hydrocinnamic acids, 2-phenyl benzoic acids, 2-phenyl phenols, benzyl sulfonates and ether-based scaffolds. The post-synthetic modification of -alkynylated arenes is also demonstrated through DG-removal as well as functional group interconversion.

Citing Articles

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

Dutta U, Prakash G, Devi K, Borah K, Zhang X, Maiti D Chem Sci. 2023; 14(41):11381-11388.

PMID: 37886091 PMC: 10599460. DOI: 10.1039/d3sc03528j.

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