Copper Catalyzed Benzylic Sp C-H Alkenylation

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2024 Oct 11

PMID 39391381

Authors

Ting-An Chen

Richard J Staples

Timothy H Warren

Affiliations

Soon will be listed here.

Abstract

The prenyl group is present in numerous biologically active small molecule drugs and natural products. We introduce benzylic C-H alkenylation of substrates Ar-CH with alkenylboronic esters (CH)OB-CH[double bond, length as m-dash]CMe as a pathway to form prenyl functionalized arenes Ar-CHCH[double bond, length as m-dash]CMe. Mechanistic studies of this radical relay catalytic protocol reveal diverse reactivity pathways exhibited by the copper(ii) alkenyl intermediate [Cu]-CH[double bond, length as m-dash]CMe that involve radical capture, bimolecular C-C bond formation, and hydrogen atom transfer (HAT).

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