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One‐Shot Radical Cross Coupling Between Benzyl Alcohols and Alkenyl Halides Using Ni/Ti/Mn System
Author(s) -
Suga Takuya,
Takahashi Yuuki,
Ukaji Yutaka
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202000945
Subject(s) - chemistry , homolysis , steric effects , halide , coupling reaction , catalysis , photochemistry , medicinal chemistry , organic chemistry , radical
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.