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One-Pot Alkene Hydroboration/Palladium-Catalyzed Migratory Suzuki–Miyaura Cross-Coupling
ACS Catalysis ( IF 12.9 ) Pub Date : 2020-08-14 , DOI: 10.1021/acscatal.0c02755
Yann Baumgartner 1 , Olivier Baudoin 1
Affiliation  

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.

中文翻译:

一锅烯烃加氢硼化/钯催化的迁移铃木-宫浦交叉偶联

链走是实现远离功能团的C–H键功能化的有效方法。尽管在过去的几年中开发了各种Pd催化的迁移交叉偶联剂,但仍然无法实现流行的Suzuki-Miyaura交叉偶联剂的高效迁移形式的设计。本文报道了一种一锅法,该方法包括烯烃硼氢化和所得烷基硼酸中间体的迁移Suzuki-Miyaura偶联。通过使用P(t -Bu)2获得了对初始烯烃的苄基位置的高区域选择性我作为配体和一个邻位取代的芳基亲电试剂。证明了从烯烃的位置和几何异构体的区域收敛性和远距离迁移。机理研究表明,迁移是通过部分可逆的非离解机制发生的。
更新日期:2020-09-20
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