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C–O Functionalization of α-Oxyboronates: A Deoxygenative gem-Diborylation and gem-Silylborylation of Aldehydes and Ketones

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    C–O Functionalization of α-Oxyboronates: A Deoxygenative gem-Diborylation and gem-Silylborylation of Aldehydes and Ketones
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    † State Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou 730000, P. R. China
    ‡ School of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400030, P. R. China
    *[email protected]
    *[email protected]
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    Cite this: J. Am. Chem. Soc. 2017, 139, 14, 5257–5264
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    https://doi.org/10.1021/jacs.7b02518
    Published March 17, 2017
    Copyright © 2017 American Chemical Society
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    Abstract

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    A deoxygenative gem-diborylation and gem-silylborylation of aldehydes and ketones is described. The key for the success of this transformation is the base-promoted C–O bond borylation or silylation of the generated α-oxyboronates. Experimental and theoretical studies exhibit that the C–O bond functionalization proceeds via an intramolecular five-membered transition-state (9-ts) boryl migration followed by a 1,2-metalate rearrangement with OBpin as a leaving group. The transformation occurs with an inversion on the carbon center. Direct conversion of aldehydes and ketones to gem-diboron compounds was achieved by combining copper catalysis with this base-promoted C-OBpin borylation. Various aldehydes and ketones were deoxygenatively gem-diborylated. gem-Silylborylation of aldehydes and ketones were achieved by a stepwise operation, in which B2pin2 initially react with those carbonyls followed by a silylation with Bpin-SiMe2Ph.

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    This article is cited by 151 publications.

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    Cite this: J. Am. Chem. Soc. 2017, 139, 14, 5257–5264
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