期刊
ACS CATALYSIS
卷 8, 期 3, 页码 2582-2588出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.7b03118
关键词
reaction mechanism; transition state; DFT study; fluorine; hypervalent compounds
资金
- Deutsche Bundesstiftung Umwelt
- King Abdullah University of Science and Technology (KAUST)
A chiral iodoarene organocatalyst for the catalytic asymmetric fluorination has been developed. The catalyst was used in the asymmetric fluorination of carbonyl compounds, providing the products with a quaternary stereocenter with high enantioselectivities. Chiral hypervalent iodine difluoride intermediates were generated in situ by treatment of the catalyst with an oxidant and hydrogen fluoride as fluoride source. As such, the alpha-fluorination of a carbonyl compound was achieved with a nucleophilic fluorine source. A combined computational and experimental approach provided insight into the reaction mechanism and the origin of enantioselectivity.
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