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Photoinduced Deaminative Borylation of Alkylamines

  • Jingjing Wu
    Jingjing Wu
    School of Chemistry, University of Bristol, Cantock’s Close, Bristol BS8 1TS, United Kingdom
    More by Jingjing Wu
  • Lin He
    Lin He
    School of Chemistry, University of Bristol, Cantock’s Close, Bristol BS8 1TS, United Kingdom
    More by Lin He
  • Adam Noble
    Adam Noble
    School of Chemistry, University of Bristol, Cantock’s Close, Bristol BS8 1TS, United Kingdom
    More by Adam Noble
  • , and 
  • Varinder K. Aggarwal*
    Varinder K. Aggarwal
    School of Chemistry, University of Bristol, Cantock’s Close, Bristol BS8 1TS, United Kingdom
    *[email protected]
Cite this: J. Am. Chem. Soc. 2018, 140, 34, 10700–10704
Publication Date (Web):August 9, 2018
https://doi.org/10.1021/jacs.8b07103
Copyright © 2018 American Chemical Society

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    Abstract

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    An operationally simple deaminative borylation reaction of primary alkylamines has been developed. The formation of electron-donor–acceptor complexes between N-alkylpyridinium salts and bis(catecholato)diboron enables photoinduced single-electron transfer and fragmentation to carbon-centered radicals, which are subsequently borylated. The mild conditions allow a diverse range of readily available alkylamines to be efficiently converted into synthetically valuable alkylboronic esters under catalyst-free conditions.

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