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4,4'-Bipyridyl-Catalyzed Reduction of Nitroarenes by Bis(neopentylglycolato)diboron.

Hiromu HosoyaLuis C Misal CastroIbrahim SultanYumiko NakajimaToshimichi OhmuraKazuhiko SatoHayato TsurugiMichinori SuginomeKazushi Mashima
Published in: Organic letters (2019)
4,4'-Bipyridyl worked as an organocatalyst for the reduction of nitroarenes by bis(neopentylglycolato)diboron (B2nep2), followed by hydrolysis to give the corresponding anilines. This reduction proceeded under aerobic conditions without any prepurification of substrates and reagents. We found broad functional group tolerance and compatibility for O- and N-protecting groups under the reaction conditions. The key in this catalytic system was the addition of B2nep2 to 4,4'-bipyridyl to form N,N'-bis[(neopentylglycolato)boryl]-4,4'-bipyridinylidene as a deoxygenating reagent of nitroarenes.
Keyphrases
  • ionic liquid
  • room temperature
  • high intensity
  • electron transfer