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

2025/01/24 by Benjamin N. Ahern, Daniel J. Weix · 1 voice
Chemistry · #Oxidative Organic Chemistry Reactions #Chemical Synthesis and Reactions #Vanadium and Halogenation Chemistry

paper · doi:10.1021/acs.orglett.4c04676

openalex publication_date 2025/01/24 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/25

Abstract

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.

Citations

• Cross-Electrophile Couplings of Activated and Sterically Hindered Halides and Alcohol Derivatives
• Metallaphotoredox-enabled deoxygenative arylation of alcohols

Discussions

• Our work on in-situ generation of alkyl chlorides using Ghosez’s reagent and coupling with aryl chlorides is now online at Org. Lett. Congrats Ben! @pubs.acs.org Check it out! doi.org/10.1021/acs.org [bsky, 5 points, 0 comments]

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