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Difunctionalization of ketones via gem-bis(boronates) to synthesize quaternary carbon with high selectivity

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Abstract

All-carbon quaternary centres are significant and prevalent structural frameworks but their preparation routes are rare and challenging, especially methods with common substrates. Herein, we report a convenient process to construct all-carbon quaternary centres from ketones via the diborylation process and Suzuki–Miyaura cross-coupling reaction. This methodology, which simultaneously introduces two different kinds of electrophilic structures, exhibits a large substrate scope and high functional group tolerance. The reaction products with aldehyde and allylic groups have proved to be versatile synthons to prepare complex molecules crucial for natural product synthesis.

Graphical abstract: Difunctionalization of ketones via gem-bis(boronates) to synthesize quaternary carbon with high selectivity

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Publication details

The article was received on 28 Sep 2018, accepted on 05 Nov 2018 and first published on 05 Nov 2018


Article type: Communication
DOI: 10.1039/C8CC07781A
Citation: Chem. Commun., 2018, Advance Article
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    Difunctionalization of ketones via gem-bis(boronates) to synthesize quaternary carbon with high selectivity

    P. Zheng, Y. Zhai, X. Zhao and T. XU, Chem. Commun., 2018, Advance Article , DOI: 10.1039/C8CC07781A

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