Electrochemically Driven Deoxygenative Borylation of Alcohols and Carbonyl Compounds.

Weiyang Guan, Yejin Chang, Song Lin
Author Information
  1. Weiyang Guan: Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14850, United States.
  2. Yejin Chang: Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14850, United States.
  3. Song Lin: Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14850, United States. ORCID

Abstract

We present a new, unified approach for the transformation of benzylic and allylic alcohols, aldehydes, and ketones into boronic esters under electroreductive conditions. Key to our strategy is the use of readily available pinacolborane, which serves both as an activator and an electrophile by first generating a redox-active trialkylborate species and then delivering the desired deoxygenatively borylated product. This strategy is applicable to a variety of substrates and can be employed for the late-stage functionalization of complex molecules.

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Grants

  1. R01 GM130928/NIGMS NIH HHS

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