-C-H Functionalization of Phenylethyl and Benzylic Alcohol Derivatives Pd/NBE Relay Catalysis

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2024 Sep 13

PMID 39268204

Authors

Hua-Chen Shen

Jian-Jun Li

Peng Wang

Jin-Quan Yu

Affiliations

Soon will be listed here.

Abstract

The transition metal-catalyzed -C-H functionalization of alcohols and their hydroxylamine derivatives remains underdeveloped. Herein, we report an efficient -C-H arylation of both phenylethyl and benzylic alcohols and their hydroxylamine derivatives using a readily removable oxime ether directing group. Using electronically activated 2-carbomethoxynorbornene as the transient mediator and 3-trifluoromethyl-2-pyridone as the enabling ligand, this reaction features a broad substrate scope and good functional group tolerance. More importantly, with this oxime-directed -C-H functionalization, this method provides a dual approach for efficient access to both -substituted alcohols and hydroxylamines using two sets of simple deprotection conditions. This protocol leads to the efficient synthesis of bioactive compounds possessing promising reactivities for the treatment of pulmonary fibrosis.

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