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Metal-free deoxygenation and reductive disilylation of nitroarenes by organosilicon reducing reagents
A metal-free deoxygenation and reductive disilylation of nitroarenes was achieved using N,N?-bis(trime-thylsilyl)-4,4?-bipyridinylidene (1) under mild and neutral reaction conditions, and a broad functional group tolerance was possible in this reaction. Mono-deoxygenation, giving a synthetically valuable N,O-bis(trimethylsilyl)phe-nylhydroxylamine (7a) as a readily available and safe phenylnitrene source from nitrobenzene, and double-deoxy-genation, giving N,N-bis(trimethylsilyl)anilines 8, were easily controlled by varying the amounts of 1 and reaction temperature as well as adding dibenzothiophene (DBTP). Reaction of 2-arylnitrobenzenes with 1 resulted in the formation of the corresponding carbazoles 14 via in situ-gen-erated phenylnitrene species derived by thermolysis of N,O-bis(trimethylsilyl)phenylhydroxylamines 7, followed by their subsequent intramolecular C H insertion. In addition, the intramolecular N N coupling reaction proceeded in the reduction of 2,2?-dinitrobiphenyl derivatives by 1, giving the corresponding benzo[c]cinnolines.
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Reference£º
Benzofuran – Wikipedia,
Benzofuran | C8H3865O – PubChem