FeCl3-Catalyzed aminohalogenation of arylmethylenecyclopropanes and arylvinylidenecyclopropanes and corresponding mechanistic studies.
[reaction: see text] The aminochlorination of methylenecyclopropanes (MCPs) 1 and vinylidenecyclopropanes (VCPs) has been explored with use of FeCl(3) (20 mol %) as a Lewis acid catalyst in acetonitrile under convenient mild conditions. The stereochemistry has been unambiguously confirmed by X-ray structural analysis. The aziridinium-based mechanism, accounting for both regio- and stereoselectivity, has been carefully studied. A linear free-energy relationship study of this reaction confirms consistency with the Hammet equation.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, 354 Fenglin Lu, Shanghai 200032, China.
Qingjiang
Q
Li
Min
M
Shi
Cody
C
Timmons
Guigen
G
Li