Transition-metal-free decarbonylative alkylation towards N-aryl α-hydroxy amides via triple C–C bond cleavages and their selective deuteration

We disclose a transition-metal-free decarbonylative alkylation reaction for the synthesis of N-aryl alpha-hydroxy amides via precise cleavages and reorganizations of three C-C sigma bonds. For the first time, a medium-sized cycloalkyl was used as a leaving group to initiate the decarbonylative alkylation process. We also demonstrate the concept of "one-pot" inert C-C bond activation/deuteration. This strategy allows the formation of alpha,beta-deuterated hydroxyamides by using DMSO-d(6) as a solvent.