Copper-catalyzed allylic substitution of nitroally derivatives with Grignard reagents

Abstract

Grignard reagents engage with nitroallyl derivatives in the presence of copper (I) salts to promote allylic substitution of the nitro group. The reaction is particularly effective with aryl Grignards and unsubstituted nitroallyl compounds but is also applicable to diversely substituted nitroallyl derivatives and both alkyl and vinyl Grignards. A mechanism involving a Cu(I)/Cu(III) catalytic cycle is proposed for this transformation.