Hosoya Hiromu, Misal Castro Luis C, Sultan Ibrahim, Nakajima Yumiko, Ohmura Toshimichi, Sato Kazuhiko, Tsurugi Hayato, Suginome Michinori, Mashima Kazushi
Department of Chemistry, Graduate School of Engineering Science , Osaka University , Osaka 560-8531 , Japan.
Interdisciplinary Research Center for Catalytic Chemistry , National Institute of Advanced Industrial Science and Technology (AIST) , Ibaraki 305-8565 , Japan.
Org Lett. 2019 Dec 20;21(24):9812-9817. doi: 10.1021/acs.orglett.9b03419. Epub 2019 Oct 30.
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.
4,4'-联吡啶作为一种有机催化剂，用于双(新戊二醇基)二硼(Bnep)还原硝基芳烃，随后水解得到相应的苯胺。该还原反应在有氧条件下进行，无需对底物和试剂进行任何预纯化。我们发现在反应条件下，该体系对O-和N-保护基具有广泛的官能团耐受性和兼容性。该催化体系的关键在于将Bnep添加到4,4'-联吡啶中，形成,'-双[(新戊二醇基)硼基]-4,4'-联吡啶叉作为硝基芳烃的脱氧试剂。
