Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 16, Pages 10451-10465Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c00415
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Funding
- National Institutes of Health [R35 GM124661]
- Madison and Lila Self Graduate Fellowship
- NIH [S10OD016360, S10RR024664]
- NSF [9977422, 0320648]
- NIH Center Grant [P20GM103418]
- NSF Chemical Instrumentation Grant [0946883]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [9977422, 0946883] Funding Source: National Science Foundation
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gem-Difluoroalkenes represent valuable synthetic handles for organofluorine chemistry; however, most reactions of this substructure proceed through reactive intermediates prone to eliminate a fluorine atom and generate monofluorinated products. Taking advantage of the distinct reactivity of gem-difluoroalkenes, we present a cobalt-catalyzed regioselective unsymmetrical dioxygenation of gem-difluoroalkenes using phenols and molecular oxygen, which retains both fluorine atoms and provides beta-phenoxy-beta,beta-difluorobenzyl alcohols. Mechanistic studies suggest that the reaction operates through a radical chain process initiated by Co(II)/O-2/phenol and quenched by the Co-based catalyst. This mechanism enables the retention of both fluorine atoms, which contrasts most transition-metal-catalyzed reactions of gem-difluoroalkenes that typically involve defluorination.
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