Use of a benzyl ether as a traceless hydrogen donor in the anti-Markovnikov hydrofunctionalization of alkenes with xanthates†
Hirohito Hayashi,Atsushi Kaga,Bin Wang,Fabien Gagosz,Shunsuke Chiba
Chemical Communications Pub Date : 06/13/2018 00:00:00 , DOI:10.1039/C8CC02971G
Abstract

A new protocol for the anti-Markovnikov hydrofunctionalization of alkenyl alcohol O-Bn ethers was developed using xanthates as functionalizing agents in the presence of lauroyl peroxide as a radical initiator and a stoichiometric oxidant. The benzyl group serves as a traceless hydrogen donor in the remote radical hydrogen atom transfer event during the process.

Graphical abstract: Use of a benzyl ether as a traceless hydrogen donor in the anti-Markovnikov hydrofunctionalization of alkenes with xanthates