Sigmatropic rearrangements of B(MIDA)-propargylic alcohols towards the diverse synthesis of α-functionalized organoborons  

作　　者：Jiasheng Qian Li-Cai Liu Zhi-Hao Chen Yuan Liu Yin Li Qingjiang Li Honggen Wang 

机构地区：[1]Guangdong Key Laboratory of Chiral Molecule and Drug Discovery,School of Pharmaceutical Sciences,Sun Yat-Sen University,Guangzhou,510006,China

出　　处：《Science China Chemistry》2024年第2期568-575,共8页中国科学（化学英文版）

基　　金：supported by the National Natural Science Foundation of China (22022114,21971261);the Local Innovative and Research Teams Project of Guangdong Pearl River Talents Program(2017BT01Y093);Guangdong Basic Research Center of Excellence for Functional Molecular Engineering。

摘　　要：α-Functionalized organoborons are useful building blocks and key structural elements in functional molecules.Their previous synthesis relied on the famous Matteson reaction or the late-stage borylative modification of alkynes or alkenes.Recently,the synthetic transformation of borylated building blocks offers another useful strategy and is currently actively explored.We report herein that B(MIDA)-propargylic alcohols(BPAs) are a useful type of borylated building blocks.Bearing two complementary functional group handles(alkyne and hydroxyl) in close proximity,the redox-neutral [3,3] and [2,3] sigmatropic rearrangements of BPAs allow the efficient synthesis of several types of α-functionalized boronates,including α,β-unsaturated acylborons,α-S/P-substituted allenylborons,boryl-substituted thiazoles and a borylated α,β-unsaturated hydrazine,some of which are otherwise challenging targets using other synthetic methods.

关 键 词：ORGANOBORON diverse synthesis sigmatropic rearrangement HETEROARENE AMIDE 

分 类 号：TQ263.1[化学工程—有机化工]