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Updated: Jun 10, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Copper catalyzed benzylic sp3 C-H alkenylation
Ting-An Chen1,2, Richard J Staples2, Timothy H Warren2
1Department of Chemistry, Georgetown University Washington D.C. 20057 USA.
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-CH2CH[double bond, length as m-dash]CMe2. Mechanistic studies of this radical relay catalytic protocol reveal diverse reactivity pathways exhibited by the copper(ii) alkenyl intermediate [CuII]-CH[double bond, length as m-dash]CMe2 that involve radical capture, bimolecular C-C bond formation, and hydrogen atom transfer (HAT).
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