烯烃
硼氢化
区域选择性
化学
钯
芳基
催化作用
电泳剂
配体(生物化学)
组合化学
迁移插入
有机硼化合物
硼酸化
立体化学
有机化学
烷基
受体
生物化学
作者
Yann Baumgartner,Olivier Baudoin
出处
期刊:ACS Catalysis
日期:2020-08-14
卷期号:10 (18): 10508-10515
被引量:20
标识
DOI:10.1021/acscatal.0c02755
摘要
Chain-walking is a powerful approach toward the functionalization of C–H bonds remote to a functional group. Whereas various Pd-catalyzed migratory cross-couplings have been developed in the past years, the design of an efficient migratory version of the popular Suzuki–Miyaura cross-coupling has remained elusive. The current article reports a one-pot procedure consisting of alkene hydroboration and migratory Suzuki–Miyaura coupling of the resulting alkylboronic acid intermediate. A high regioselectivity for the benzylic position of the initial alkene was achieved by using P(t-Bu)2Me as the ligand and an ortho-substituted aryl electrophile. Regioconvergence from alkene positional and geometrical isomers and long-range migration were demonstrated. Mechanistic investigations indicated that the migration occurs through a partially reversible, nondissociative mechanism.
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