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

页码：11498 / 11502

页数：5