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

Hiromu Hosoya, Luis C. Misal Castro, Ibrahim Sultan, Yumiko Nakajima, Toshimichi Ohmura*, Kazuhiko Sato*, Hayato Tsurugi*, Michinori Suginome* and Kazushi Mashima*

*Kyoto University, Kyoto 615-8510; AIST, Ibaraki 305-8565; Osaka University, Osaka 560-8531, Japan, Email: ohmuraEsbchem.kyoto-u.ac.jp, k.satoaist.go.jp, tsurugichem.es.osaka-u.ac.jp, suginomesbchem.kyoto-u.ac.jp, mashimachem.es.osaka-u.ac.jp

H. Hosoya, L. C. M. Castro, I. Sultan, Y. Nakajima, T. Ohmura, K. Sato, H. Tsurugi, M. Suginome, K. Mashima, Org. Lett., 2019, 21, 9812-9817.

DOI: 10.1021/acs.orglett.9b03419

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Abstract

4,4′-Bipyridine worked as an organocatalyst for the reduction of nitroarenes by bis(neopentylglycolato)diboron (B2nep2), followed by hydrolysis to give the corresponding anilines with broad functional group tolerance.


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proposed mechanism

Key Words

reduction of nitro compounds, bis(neopentylglycolato)diboron, organocatalysis

ID: J54-Y2019