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Palladium-Catalyzed Unimolecular Fragment Coupling of N -Allylamides via Elimination of Isocyanate

2022; American Chemical Society; Volume: 144; Issue: 24 Linguagem: Inglês

10.1021/jacs.2c04527

1943-2984

Ryoma Shimazumi, Riku Tanimoto, Takuya Kodama, Mamoru Tobisu,

Catalytic C–H Functionalization Methods

Transition metal-catalyzed unimolecular fragment coupling (UFC) is defined as processes that forge new chemical bonds through the extrusion of molecules, such as CO and CO2, and the subsequent recombination of the remaining fragments. Herein, we report on a new UFC reaction that involves the palladium-catalyzed elimination of an isocyanate fragment from an amide, with the formation of carbon–carbon and carbon–heteroatom bonds. An organometallic intermediate that is relevant to the catalytic reaction was characterized by X-ray crystallography. This UFC reaction enables the late-stage transformation of an amide functionality, allowing amides to be used as a convertible directing or protecting group.