Oxidative Geminal Functionalization of Organoboron Compounds

Authors

  • Zhi He,

    1. Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George St. Toronto, ON, M5S 3H6 (Canada)
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  • Piera Trinchera,

    1. Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George St. Toronto, ON, M5S 3H6 (Canada)
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  • Dr. Shinya Adachi,

    1. Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George St. Toronto, ON, M5S 3H6 (Canada)
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  • Jeffrey D. St. Denis,

    1. Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George St. Toronto, ON, M5S 3H6 (Canada)
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  • Prof. Dr. Andrei K. Yudin

    Corresponding author
    1. Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George St. Toronto, ON, M5S 3H6 (Canada)
    • Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George St. Toronto, ON, M5S 3H6 (Canada)
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  • We would like to thank Natural Science and Engineering Research Council (NSERC) and Canadian Institutes of Health Research (CIHR) for financial support.

Abstract

original image

Excellent tolerance: Stable acylboronates equipped with N-methyliminodiacetyl (MIDA) boryl groups ([B]) were prepared by using a sequence of oxidative manipulations at the boron-bound carbon center (green in scheme). Chemoselective transformations of these acylated organoboron building blocks yielded a range of multifunctionalized boron derivatives and supplied access to valuable borylated heterocycles (see scheme).

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