Nitrosobenzene was first synthesized by Bayer at the end of nineteenth century.[1] Since then, it has been considered as a useful reagent to deliver several nitrogen- and oxygen-containing molecules. The dual electrophilic sites of nitrosoarene provide attractive routes for the C–N and/or C–O bond forming reactions. But the use of nitrosoarene as catalyst has not been explored prior to our proposed work.
To explore the catalytic activity of nitrosoarenes, aromatic amines and (hetero)arenes, such as indoles and pyrroles, are regioselectively sulfinylated under mild aerobic conditions using nitrosoarenes as a redox-catalyst. The nitrosoarene is involved in the electron transfer process with arenes to generate a crucial arene radical cation intermediate for C–H sulfinylation. This methodology requires no directing group, can be scaled up easily and is applicable for the late-stage functionalization of drug molecules and natural products with high regioselectivity.[2]
At the same line we have reported a rare metal-free nucleophilic nitrosoarene catalysis accompanied by highly hydrogen-bond-donor (HBD) solvent, HFIP, organocatalytically converts arylmethyl halides to aromatic carbonyls. This protocol offers an effective means to access a diverse array of aromatic carbonyls with good chemoselectivity under mild reaction conditions. The activation of arylmethyl halides by HFIP to generate stable carbocation and autoxidation of in situ generated hydroxylamine to nitrosoarene in the presence of atmospheric O2 are the keys to success.[3]

Nitrosoarene Catalyzed C–heteroatom bond Forming Reactions

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27th CRSI National Symposium in Chemistry

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