Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 7, Issue 18, Pages 2618-2627Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0qo00773k
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- Innovation & Entrepreneurship Talents Plan of Jiangsu Province
- National Natural Science Foundation of China [21972064]
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An efficient method for the construction ofgem-difluoroallylsilanes with high enantiomeric excessviaa copper-catalysed defluorosilylation of trifluoromethylated alkenes with silylboronates is described. The key to this high enantioselectivity is the careful selection of NaOH as the base and using a triazolium-based chiral N-heterocyclic carbene (NHC) as a ligand in the presence of a copper catalyst. The reaction conditions are mild, and excellent functional group compatibility is observed. This strategy addresses the limitations of the previously described base-mediated defluorosilylation under transition metal-free conditions, which can lead to erosion of the enantioselectivity. The synthetic utilities of the obtainedgem-difluoroallylsilanes are also presented. Computational and experimental data suggest that the reaction proceeds through the enantioselective insertion of silyl-Cu/NHC species into the double bond of trifluormethyl alkenes and the Cu-mediated beta-F elimination steps.
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