Difluorocarbene-Triggered Acyl Rearrangement Reaction: A Strategy for the Direct Introduction of the
Haitao Cui1, Caijin Ban1, Fengting Zhu1
1Guangxi Key Laboratory of Natural Polymer Chemistry and Physics, Nanning Normal University, Nanning, Guangxi 530100, People's Republic of China.
Abstract:
A novel metal- and catalyst-free dearomative reaction of 2-oxypyridines to construct gem-difluoromethylenated N-substituted 2-pyridones has been developed. The reaction involves an attractive acyl rearrangement from O to CF2 of difluorocarbene-derived pyridinium ylides, which provides a new strategy for the direct introduction of the gem-difluoromethylene group with high efficiency and selectivity as well as broad substrate scope. Gram-scale synthesis and synthetic transformations have also been demonstrated.
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