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.
Sirois, J. J., & DeBoef, B. (2015). Transition-metal free umpolung carbon-nitrogen vs. carbon-chlorine bond formation. Tetrahedron Letters, 56(7), 5610-5612. doi: 10.1016/j.tetlet.2015.08.053