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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=CMe2 as a pathway to form prenyl functionalized arenes Ar-CH2CH=CMe2. Mechanistic studies of this radical relay catalytic protocol reveal diverse reactivity pathways exhibited by the copper(II) vinyl intermediate [CuII]-CH=CMe2 that involve radical capture, bimolecular C-C bond formation, and hydrogen atom transfer (HAT).
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Chen et al. (2024) studied this question.
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