A 1,2-difunctionalization
of an unactivated alkene, imidoyl-carbamoylation,
has been developed through a palladium-catalyzed four-component cascade
reaction involving aryl iodide, alkenyl isocyanide, CO, and amine.
Continuous migratory insertion of three different functionalities
to the Pd(II) intermediate generated from the previous step takes
place in a well-defined sequence. Four chemical bonds, including three
C–C bonds and one C–N bond, are formed in this cascade
process, leading to a convenient and convergent access to acetamides
substituted with five- to seven-membered cyclic ketoimines. In addition,
an extra C–N bond is formed through in situ or postreaction cyclization of the amido NH to the ketoimine moiety,
providing a facile one-pot access to pyrrolo-fused heterocycles.
An unprecedented tandem carbonylation/aminocarbonylation triggered by palladium-catalyzed enantioselective Heck-type exocyclopalladation delivering chiral heterocyclic α-ketoamides has been developed. The uncommon double CO insertion into the σ-alkylpalladium intermediate takes place selectively under...
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