Date of Original Version
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 formation involving N-chloroamines and organometallic reagents. Knowing the yields of uncatalyzed reactions will be useful when determining the success of future catalytic methods.
John J. Sirois, Brenton DeBoef. (2015). "Transition-metal free umpolung carbon-nitrogen vs. carbon-chlorine bond formation." Tetrahedron Letters.