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Palladium-catalyzed intramolecular aminofluorination of unactivated alkenes
Tao Wu1, Guoyin Yin, Guosheng Liu
1State Key Laboratory of Organometallics Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, 354 Fenglin Road, Shanghai, China, 200032.
Abstract:
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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