Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 144, Issue 24, Pages 11033-11043Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.2c04527
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Funding
- JSPS KAKENHI [JP21H04682]
- JST SPRING [JPMJSP2138]
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This study reports a new UFC reaction that involves the palladium-catalyzed elimination of an isocyanate fragment from an amide, resulting in the formation of carbon-carbon and carbon-heteroatom bonds. This reaction enables the late-stage transformation of the amide functionality.
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.
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