Formal Carbon Insertion of N-Tosylhydrazone into B-B and B-Si Bonds: gem-Diborylation and gem-Silylborylation of sp³ Carbon

Huan Li, Xianghang Shangguan, Zhikun Zhang, Shan Huang, Yan Zhang and Jianbo Wang*

*Beijing National Laboratory of Molecular Sciences (BNLMS), College of Chemistry, Peking University, Beijing 100871, China, Email: wangjbpku.edu.cn

H. Li, X. Shangguan, Z. Zhang, S. Huang, Y. Zhang, J. Wang, Org. Lett., 2014, 16, 448-451.

DOI: 10.1021/ol403338s

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Abstract

A convenient method for the synthesis of 1,1-diboronates from the corresponding N-tosylhydrazones is also applicable to 1-silyl-1-boron compounds. Derivatization and consecutive Pd-catalyzed cross-coupling reactions with 1,1-boronates were also explored, demonstrating the synthetic potential of 1,1-diboronates.

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Key Words

alkylboronates, alkylsilanes, 1,1-silylboronates

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ID: J54-Y2014