One-shot cross coupling achieves efficient synthesis of allylbenzene derivatives using benzyl alcohols and alkenyl halides, suggesting a new synthetic strategy.
A “one‐shot” cross coupling between benzyl alcohols and alkenyl halides has been established. A combination of low‐valent Ti‐mediated C−OH homolysis and the prominent chemistry of Ni‐based radical catalysis afforded the desired cross‐coupled product with good efficiency. The reaction proceeded regardless of the electronic property of benzyl alcohols, and Ar−B bond remained intact throughout the reaction. Alkenyl bromides with various substitution patterns were applicable to this reaction. Attempts for utilizing sterically demanding tri‐substituted alkenes indicated that the steric hinderance mainly inhibited the radical‐trapping by Ni species. This reaction can be a simple and efficient strategy for synthesizing densely substituted allylbenzene derivatives.
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Suga et al. (2020) studied this question.
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