Rhodium(i)-catalyzed C6-selective C-H Alkenylation and Polyenylation of 2-pyridones with Alkenyl and Conjugated Polyenyl Carboxylic Acids

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2020 Feb 15

PMID 32055363

Citations 3

Authors

Haoqiang Zhao

Xin Xu

Zhenli Luo

Lei Cao

Bohan Li

Huanrong Li

Lijin Xu

Qinghua Fan

Patrick J Walsh

Affiliations

Soon will be listed here.

Abstract

A versatile Rh(i)-catalyzed C6-selective decarbonylative C-H alkenylation of 2-pyridones with readily available, and inexpensive alkenyl carboxylic acids has been developed. This directed dehydrogenative cross-coupling reaction affords 6-alkenylated 2-pyridones that would otherwise be difficult to access using conventional C-H functionalization protocols. The reaction occurs with high efficiency and is tolerant of a broad range of functional groups. A wide scope of alkenyl carboxylic acids, including challenging conjugated polyene carboxylic acids, are amenable to this transformation and no addition of external oxidant is required. Mechanistic studies revealed that (1) BocO acts as the activator for the transformation of the carboxylic acids into anhydrides before oxidative addition by the Rh catalyst, (2) a decarbonylation step is involved in the catalytic cycle, and (3) the C-H bond cleavage is likely the turnover-limiting step.

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