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

Research paper by Hiromu H Hosoya, Luis C LC Misal Castro, Ibrahim I Sultan, Yumiko Y Nakajima, Toshimichi T Ohmura, Kazuhiko K Sato, Hayato H Tsurugi, Michinori M Suginome, Kazushi K Mashima

Indexed on: 28 Apr '21Published on: 31 Oct '19Published in: Organic Letters



Abstract

4,4'-Bipyridyl worked as an organocatalyst for the reduction of nitroarenes by bis(neopentylglycolato)diboron (Bnep), 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 Bnep to 4,4'-bipyridyl to form ,'-bis[(neopentylglycolato)boryl]-4,4'-bipyridinylidene as a deoxygenating reagent of nitroarenes.