Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 131, Issue 45, Pages 16354-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja9076588
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Funding
- Chinese Academy of Science
- National Natural Science Foundation of China [20821002, 20872155, 20972175]
- National Basic Research Program of China [973-2009CB825300]
- Science and Technology Commission of the Sharlghai Municipality [08PJ1411600, 08dj1400100]
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A novel palladium-catalyzed intramolecular oxidative aminofluorination of unactivated alkenes has been developed, in which AgF was used as a key fluorinating reagent and PhI(OPiv)(2) as oxidant. The reaction afforded vicinal fluoroamine products with very high regioselectivity. A Pd(II/IV) catalytic cycle was proposed, and preliminary mechanistic studies indicated that direct reductive elimination of Pd(IV) intermediates is favored, albeit competing with S(N)2 nucleophilic attack by fluorine, to form a C-F bond.
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