Metal-Free Synthesis of gem-Silylboronate Esters and Their Pd(0)-Catalyzed Cross-Coupling with Aryliodides

Metal-Free Synthesis of gem-Silylboronate Esters and Their Pd(0)-Catalyzed Cross-Coupling with Aryliodides
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DOI:
10.1039/c9ob01006h
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发表时间:
2019
期刊:
Organic & Biomolecular Chemistry
影响因子:
--
通讯作者:
Jianbo Wang
Jianbo Wang
中科院分区:
--
文献类型:
--
作者:
Chaoqiang Wu;Zhicheng Bao;Xing Xu;Jianbo Wang

文献摘要

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A transition-metal-free method for the synthesis of gem-silylboronate esters with arylboronic acids and trimethylsilyldiazomethane (TMSCHN2) has been developed. This transformation is a straightforward homologation of arylboronic acids and features wide substrate scope and good functional-group tolerance. The gem-silylboronate esters undergo efficient Suzuki–Miyaura cross-coupling with aryliodides and the silyl group of the product can be further functionalized. Tertiary carbon centers with different substituents can be constructed successfully by selective and sequential functionalization.