ATRA-like alkylation–peroxidation of alkenes with trichloromethyl derivatives by the combination of tBuOOH and NEt3

Abstract

A method was developed for alkylation–peroxidation of alkenes using tert-butyl hydroperoxide (TBHP) and chloroform under metal-free conditions. This method is a unique and innovative approach to the construction of α-tert-butylperoxy-β-dichloromethyl alkanes, employing CHCl₃ as an alkylating reagent to provide a –CHCl₂ group, and TBHP as an oxidant to provide an α-^tBuOO group. The reaction was successfully applied to carbon tetrachloride and 1,1,1-trichloroethane, and was regiospecific for terminal alkenes.