Pd-Catalyzed -C(sp)-H (Hetero)Arylation of Ketones Enabled by Transient Directing Groups

Overview

Journal ACS Catal

Publisher American Chemical Society

Date 2023 Jun 12

PMID 37305173

Authors

Yi-Hao Li

Yuxin Ouyang

Nikita Chekshin

Jin-Quan Yu

Affiliations

Soon will be listed here.

Abstract

Pd(II)-catalyzed -C(sp)-H (hetero)arylation of aliphatic ketones is developed using -amino acid as transient directing groups (TDG). A variety of aliphatic ketones were (hetero)arylated at the -position via a 5,6-membered fused cyclopalladation intermediate to afford the remotely arylated products in up to 88% yield. The crucial ligand effect of 2-pyridone is further enhanced by reducing the loading of acid additives. Consequentially, the improved reactivity of this catalytic system has also made possible the cyclic -methylene C(sp)-H arylation of ketones. Mechanistic investigtigation and comparison to the -C-H arylation of aldehydes revealed a structural insight for designing site selective TDG.

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