Work

Hydroesterification and Difunctionalization of Olefins with N-Hydroxyphthalimide Esters

Year: 2021

Type: article

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 CH 2 Cl 2 . 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. Monoacylated diols are formed from trisubstituted and tetrasubstituted olefins in the presence of water.

Source: ACS Catalysis

DOI: 10.1021/acscatal.1c03969

Authors: Lingying Leng, Joseph M. Ready

Institution: The University of Texas Southwestern Medical Center

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Welch Foundation, National Institute of General Medical Sciences

Awards: G7073091334, Chemical, Structural and Cell-Signaling Interrogation of 15-Prostanglandin Dehydrogenase in Tissue Repair and Regeneration