Palladium-Catalyzed Hydroalkoxylation of Methylenecyclopropanes

Abstract

Hydroalkoxylations proceed by a different path than transition metal catalyzed hydrostannations and hydrosilylations. In the reaction of methylenecyclopropanes 1 with alcohols 2 in the presence of Pd(0), the distal bond in the cyclopropane ring is cleaved, and allyl ether 3 is formed selectively. R(1)=n-C(7)H(15), PhCH(2)CH(2); R(2)=H, PhCH(2)CH(2); R(3)=PhCH(2), CF(3)CH(2), Et(3)Si, n-C(4)H(9), etc.