A novel aerobic oxidative Ugi-type
multicomponent reaction (MCR)
with tertiary amines was developed. The reaction was initiated by
C(sp3)–H oxidation of the amine, followed by nucleophilic
attack on the highly reactive isocyanide, generating nitrilium ion
intermediates. If these intermediates were trapped by water in the
system, α-amido amines could be delivered as the Ugi-3CR products.
If exogenous TMSN3 was added, α-tetrazolo amines
could be furnished as the first example of oxidative Ugi-azide MCR
products.
A simple and efficient Fe-catalyzed regioselective alkylation of 1,4-quinones and coumarins, using functionalized alkyl bromides as alkylating reagents, has been developed.
A method for the synthesis of 2-thiolated benzimidazoles is described starting from thiols and 1-azido-2-isocyanoarenes. The isocyano group works as an acceptor of various thio radicals, followed by denitrogenative annulation of the resulting imidoyl radical intermediates to the azido group, with nitrogen loss as the only process.
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