One-Pot Chlorination and Cross-Electrophile Coupling of Alcohols with Aryl Chlorides

Although alkyl alcohols and aryl chlorides are the two most abundant substrate pools for cross-electrophile coupling, methods to couple them remain limited. Herein we demonstrate a simple procedure for the in situ deoxychlorination of alcohols followed by XEC with aryl chlorides. A broad substrate scope can be achieved by tuning the rate of the reaction via halide exchange. Key to success is the identification of 1-chloro-N,N,2-trimethyl-1-propenylamine as a mild, noninterfering halogenation reagent.