Transition-metal free umpolung carbon-nitrogen versus carbon-chlorine bond formation

John J. Sirois, University of Rhode Island
Brenton DeBoef, University of Rhode Island


The formation of carbon-nitrogen (C-N) bonds via an umpolung substitution reaction has been achieved at -78 °C without the need for catalysts, ligands, or additives. The scope is limited to aryl Grignard reagents with N-chloroamines. The findings in this manuscript serve as a reference point for all C-N bond formations involving N-chloroamines and organometallic reagents. Knowing the yields of uncatalyzed reactions will be useful when determining the success of future catalytic methods.