Cross-selective Deoxygenative Coupling of Aliphatic Alcohols: Installation of Methyl Groups including Isotopic Labels by Nickel Catalysis

Angew Chem Int Ed Engl. 2024 Apr 11:e202403119. doi: 10.1002/anie.202403119. Online ahead of print.ABSTRACTNickel-catalyzed cross-electrophile coupling reactions of two aliphatic alcohol derivatives remain a challenge. Herein, we report a nickel-catalyzed reductive methylation reaction of aliphatic mesylates with methyl tosylate. This reaction provides straightforward access to compounds bearing aliphatic methyl groups from alkyl alcohol derivatives. Isotopically labelled substrates and reagents can be employed in the reaction to provide perdeuterated and 13C-labelled products. This transformation can be achieved by employing stoichiometric Mn reductant or electrochemically. Additionally, mechanistic experiments show that alkyl iodides are key intermediates in the transformation which undergo a stereoablative reaction via radical intermediates.PMID:38604974 | DOI:10.1002/anie.202403119

Source: Angewandte Chemie - April 11, 2024 Category: Chemistry Authors: Patricia C Lin Chloe D Wong Elizabeth R Jarvo Source Type: research