Photosensitized Anti-Markovnikov Hydroesterification of Unactivated Alkenes

Abstract

Hydrofunctionalization of alkenes represents a fundamental strategy in synthetic organic chemistry. Herein, we describe a visible-light-promoted approach for the anti-Markovnikov hydrooxygenation of unactivated alkenes. Our protocol features the utilization of a cost-effective, bench-stable, and easyto-handle oxime ester as the reagent, enabled by energy-transfer catalysis. This methodology exhibits excellent functional group tolerance and mild reaction conditions, rendering it suitable for the hydroesterification of pharmaceutically relevant molecule-derived alkenes.

Visible-light-mediated synthesis of oxime esters via multicomponent reactions of aldehydes, aryl amines, and N-hydroxyphthalimide esters

“…For example, a wide range of biologically active compounds with anticancer, 1 anti-inflammatory, 2 antifungal, 3 antioxidant and antimicrobial 4 activities contain oxime ester moieties. Additionally, oxime esters are an important scaffold for many organic synthesis processes such as C–C bond cleavage, 5 cyanoalkylation, 6 hydroesterification, 7 cross coupling, 8 sulfonylamination, 9 and cyclization. 10 Recently, oxime esters were used as photoinitiators in photoreactions for various transformations.…”