级联
钯
催化作用
激进的
赫克反应
化学
联轴节(管道)
有机化学
组合化学
材料科学
冶金
色谱法
作者
Wei Yi,Xiaoyu Xie,Jiabin Liu,Xiaoxiao Liu,Bo Zhang,Xinyi Chen,Shi-Jun Li,Yu Lan,Kai Hong
标识
DOI:10.1002/anie.202401050
摘要
Geminal bis(boronates) are versatile synthetic building blocks in organic chemistry. The fact that they predominantly serve as nucleophiles in the previous reports, however, has restrained their synthetic potential. Herein we disclose the ambiphilic reactivity of α‐halogenated geminal bis(boronates), of which the first catalytic utilization was accomplished by merging a formal Heck cross‐coupling with a highly diastereoselective allylboration of aldehydes or imines, providing a new avenue for rapid assembly of polyfunctionalized boron‐containing compounds. We demonstrated that this cascade reaction is highly efficient and compatible with various functional groups, and a wide range of heterocycles. In contrast to a classical Pd(0/II) scenario, mechanistic experiments and DFT calculations have provided strong evidence for a catalytic cycle involving Pd(I)/diboryl carbon radical intermediates.
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