Deaminative Reductive Cross-Electrophile Couplings of Alkylpyridinium Salts and Aryl Bromides

• DOI: 10.1021/acs.orglett.9b01014
• Publication Date: 2019-03-28T00:17:51Z
• Authors: Jennie Liao; Corey H. Basch; Megan E. Hoerrner; Michael R. Talley; Brian P. Boscoe; Joseph W. Tucker; Michelle R. Garnsey; Mary P. Watson
• Keywords: Manganese; Free Radicals; Pyridines; Magnesium Chloride; Pyridinium Compounds; Bromine; Boronic Acids; 01 natural sciences; Catalysis; 0104 chemical sciences; Nickel; Amines; Oxidation-Reduction

A nickel-catalyzed reductive cross-coupling of alkylpyridinium salts and aryl bromides has been developed using Mn as the reductant. Both primary and secondary alkylpyridinium salts can be used, and high functional group and heterocycle tolerance is observed, including for protic groups. Mechanistic studies indicate the formation of an alkyl radical, and controlling its fate was key to the success of this reaction.