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Iron-Catalyzed Reductive Ring Opening/gem-Difluoroallylation of Cyclopropyl Ketones
Bing Yuan1, Chang Zhang1, Haiyan Dong
1Department of Chemistry, Center for Excellence in Molecular Synthesis, University of Science and Technology of China, Hefei, Anhui 230026, P. R. China.
Abstract:
By merging C-C and C-F bond cleavage, we developed a regioselective ring opening/gem-difluoroallylation of cyclopropyl ketones with α-trifluoromethylstyrenes, which proceeds under the catalysis of iron with the combination of manganese and TMSCl as the reducing agents, providing a new entry to the synthesis of carbonyl-containing gem-difluoroalkenes. Remarkably, the ketyl radical-induced selective C-C bond cleavage and the following generation of more-stable carbon-centered radicals enable complete regiocontrol of this ring opening reaction for various substitution patterns of the cyclopropane ring.
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