Radical-Triggered Three-Component Coupling Reaction of Alkenylboronates, α-Halocarbonyl Compounds, and Organolithium Reagents: The Inverse Ylid Mechanism

被引：52
|
作者：
Tappin, Nicholas D. C. [1 ]
Gnagi-Lux, Manuel [1 ]
Renaud, Philippe [1 ]
机构：
[1] Univ Bern, Dept Chem & Biochem, Freiestr 3, CH-3012 Bern, Switzerland
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2018年 / 24卷 / 44期
基金：
瑞士国家科学基金会;
关键词：
boronic esters; inverse boron ylids; Matteson rearrangement; radical reactions; single-electron transfer; POLAR CROSSOVER REACTIONS; PRIMARY ALKYL RADICALS; BORON ATE COMPLEXES; ASYMMETRIC-SYNTHESIS; RATE CONSTANTS; ESTERS; REARRANGEMENT; CONSTRUCTION; METHODOLOGY; KETONES;
D O I：
10.1002/chem.201802384
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An operationally simple protocol to affect a radical addition to alkenylboronates that spontaneously undergo a [1,2]-metalate shift is described. Overall, the reaction is a three-component coupling of an organolithium, alkenylboronic ester, and halide which takes place with broad scope and good to excellent yields. Experimental mechanistic investigations support the formation of a boron inverse ylid intermediate.
引用
收藏
页码：11498 / 11502
页数：5
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