Phenylselenylation of Ethers using Diphenyl Diselenide–Tributylphosphine–Molecular Oxygen System under Mild Reaction Conditions

Abstract

An efficient method for phenylselenylationo f ethers using ad iphenyl diselenide-tributylphosphine-molecular oxygen system has been successfullyd eveloped. The reactions proceed under mild conditions in good to high yield. Ap lausible reaction mechanism for the phenylselenylation via C(sp 3 )ÀHa ctivation was also proposed, and at ributylphosphonium peroxide radicalw as assumed as an important intermediate in the C(sp 3 )ÀHa ctivation.

Radical selenation of C(sp3)–H bonds to asymmetric selenides and mechanistic study

“…However, because of a lack of effective synthetic methods, the direct oxidative selenation of the C(sp 3 )-H bonds of ethereal solvents is rarely reported to date. 11 The use of such simple ethers in C-Se bond forming reactions to construct higher-functionalized selenides is highly desirable but challenging.…”