Journal
ORGANIC LETTERS
Volume 21, Issue 11, Pages 4284-4288Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b01471
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Funding
- JSPS KAKENHI [JP 15H05485, 18K19078, JP 17H06092]
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A copper-catalyzed regioselective net hydroamination of 1-trifluoromethylalkenes with hydrosilanes and hydroxylamines has been developed. The judicious choice of ligand and additive suppresses the conceivable but undesired beta-F elimination of an alpha-CF3-substituted organocopper intermediate, leading to targeted alpha-trifluoromethylamines in good yields with excellent regioselectivity. Additionally, with an appropriate chiral bisphosphine ligand, the enantioselective reaction is also possible to deliver optically active alpha-trifluoromethylamines of high potential in medicinal and pharmaceutical chemistry.
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