4.8 Article

Base-Mediated Borylsilylation/Silylation of Ammonium Salts with Silylborane

Journal

ORGANIC LETTERS
Volume 23, Issue 15, Pages 5988-5992

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c02066

Keywords

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Funding

  1. National Natural Science Foundation of China [21901260]
  2. Funda-mental Research Funds for the Central Universities, Sun Yatsen University [20ykpy129]
  3. MOE Key Laboratory of Laser Life Science

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The study describes a base-mediated reaction for synthesizing geminal silylboronates with a benzylic proton under mild conditions, as well as achieving deaminative silylation of aryl ammonium salts. This strategy, featuring high efficiency, mild reaction conditions, and good functional group tolerance, provides efficient pathways for late-stage functionalization of amines.
This work describes a base-mediated borylsilylation of benzylic ammonium salts to synthesize geminal silylboronates bearing benzylic proton under mild reaction conditions. Deaminative silylation of aryl ammonium salts was also achieved in the presence of (LiOBu)-Bu-t. This strategy which is featured with high efficiency, mild reaction conditions, and good functional group tolerance provides efficient routes for late-stage functionalization of amines.

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