Hydroesterification and difunctionalization of olefins with N-hydroxyphthalimide esters.

ABSTRACT: Irradiation of aryl esters of N-hydroxyphthalimides in the presence of unactivated olefins promotes a mild and regioselective hydroesterification. Optimal results are obtained with the aid of fac-Ir(dFppy)₃ in CH₂Cl₂. Terminal and 1,1-disubstituted olefins provide primary esters, and trisubstituted olefins provide secondary esters. The anti-Markovnikov selectivity is consistent with alkyl radical intermediates, which are also indicated by the formation of cyclized products from dienes. Mono-acylated diols are formed from tri- and tetrasubstituted olefins in the presence of water.

SUBMITTER: Leng L 

PROVIDER: S-EPMC9385172 | biostudies-literature | 2021 Nov

REPOSITORIES: biostudies-literature