A feasible and effective method to synthesize α-fluoroalkenyl alcohols was reported. With the cooperation of photoredox and hydrogen atom transfer (HAT) processes, defluoroalkylations of -difluoroalkenes occurred smoothly with alcohols under visible-light irradiation. Notably, the protocols feature broad scopes, mild conditions, and validity for the late-stage functionalization of bioactive molecule derivatives. Mechanistic studies suggested that the reaction occurred through the radical coupling of the alkyl radical and the fluoroalkenyl radical.
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Photoredox Catalytic Defluoroalkylation of -Difluoroalkenes with Secondary -Alkylanilines via C-F/C-H Coupling.
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College of New Energy, State Key Laboratory of Heavy Oil Processing, China University of Petroleum (East China), 266580 Qingdao, P. R. China.
To provide fluorinated allylamines, a visible-light photocatalytic C-F/C-H coupling of easily accessible -difluoroalkenes and secondary -alkylanilines was described. The protocol proceeded under mild conditions, with excellent functional group compatibility and a broad scope including complex natural product derivatives, thus providing a green method for the preparation of high-value functionalized monofluoroalkenes. Mechanistic studies elucidated a photoredox catalyzed radical-radical coupling pathway.
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College of New Energy, State Key Laboratory of Heavy Oil Processing, China University of Petroleum (East China), 266580 Qingdao, P. R. China.
A feasible and effective method to synthesize α-fluoroalkenyl alcohols was reported. With the cooperation of photoredox and hydrogen atom transfer (HAT) processes, defluoroalkylations of -difluoroalkenes occurred smoothly with alcohols under visible-light irradiation. Notably, the protocols feature broad scopes, mild conditions, and validity for the late-stage functionalization of bioactive molecule derivatives.
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