Copper catalyzed benzylic sp3 C–H alkenylation

Ting-An Chen; Richard J. Staples; Timothy H. Warren

doi:10.1039/D4SC03430A

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Copper catalyzed benzylic sp³ C–H alkenylation†

Ting-An Chen,^ab Richard J. Staples

^b and Timothy H. Warren

*^b

Author affiliations

* Corresponding authors

^a Department of Chemistry, Georgetown University, Washington, D.C. 20057, USA

^b Department of Chemistry, Michigan State University, East Lansing, Michigan 48824, USA
E-mail: warre155@msu.edu

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-CH₃ with alkenylboronic esters (CH₂)₃O₂B–CH [double bond, length as m-dash] CMe₂ as a pathway to form prenyl functionalized arenes Ar-CH₂CHCMe₂. Mechanistic studies of this radical relay catalytic protocol reveal diverse reactivity pathways exhibited by the copper(II) alkenyl intermediate [Cu^II]-CHCMe₂ that involve radical capture, bimolecular C–C bond formation, and hydrogen atom transfer (HAT).

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Article information

DOI: https://doi.org/10.1039/D4SC03430A
Article type: Edge Article
Submitted: 25 May 2024
Accepted: 15 Sep 2024
First published: 19 Sep 2024
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry

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Chem. Sci., 2024,15, 17685-17690

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Copper catalyzed benzylic sp³ C–H alkenylation

T. Chen, R. J. Staples and T. H. Warren, Chem. Sci., 2024, 15, 17685 DOI: 10.1039/D4SC03430A

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