AI Article Synopsis
- - 4,4'-Bipyridyl effectively acted as an organocatalyst in reducing nitroarenes using bis(neopentylglycolato)diboron (Bnep), eventually converting them into anilines through hydrolysis.
- - The reaction was conducted under aerobic conditions, and there was no need to prepurify the substrates or reagents, simplifying the process.
- - The study highlighted a broad tolerance for various functional groups and protecting groups, with the critical step being the formation of a unique boryl compound by combining Bnep with 4,4'-bipyridyl.
Article 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.
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| http://dx.doi.org/10.1021/acs.orglett.9b03419 | DOI Listing |
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