An
iron-mediated highly selective C–H sulfonylmethylation
of aniline derivatives with p-toluenesulfonylmethyl
isocyanide in a mixture solvent of H2O and PEG400 under an Ar atmosphere has been realized. This transformation proceeds
with operational convenience, use of earth-abundant metal catalyst
and nontoxic media, broad substrate scope, and good functional group
tolerance. The current methodology could be applied to the regioselective
C–H sulfonylmethylation of indolines, tetrahydroquinolines,
and tertiary anilines.
A Fe(III)-catalyzed N-amidomethylation of secondary
and primary anilines with p-toluenesulfonylmethyl
isocyanide (TosMIC) in water is described. TosMIC plays dual roles
as the source of methylene as well as an amidating reagent to form
α-amino amides in this multicomponent reaction. The combination
of TosMIC and other isocyanides was also investigated to give the
desired products in acceptable yields. The current protocol features
use of iron catalyst and nontoxic media, broad substrate scope, mild
conditions, and operational simplicity.
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