Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 47, Pages 15073-15077Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201709487
Keywords
alkenes; alkylation; fluorine; photochemistry; radicals
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Funding
- NIGMS [R01 GM 113878]
- NIH [S10 OD011980]
- NIH NRSA [F32 GM117634-01]
- NSF GRFP
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Described is a facile, scalable route to access functional-group-rich gem-difluoroalkenes. Using visible-light-activated catalysts in conjunction with an arsenal of carbon-radical precursors, an array of trifluoromethyl-substituted alkenes undergoes radical defluorinative alkylation. Nonstabilized primary, secondary, and tertiary radicals can be used to install functional groups in a convergent manner, which would otherwise be challenging by two-electron pathways. The process readily extends to other perfluoroalkyl-substituted alkenes. In addition, we report the development of an organotrifluoroborate reagent to expedite the synthesis of the requisite trifluoromethyl-substituted alkene starting materials.
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