title: Transition-metal free umpolung carbon-nitrogen vs. carbon-chlorine bond formation.
abstract: 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.
authors.affiliation: Department of Chemistry, University of Rhode Island, Kingston, Rhode Island 02881.
authors.forename: John J
authors.initials: JJ
authors.lastname: Sirois
authors.affiliation: Department of Chemistry, University of Rhode Island, Kingston, Rhode Island 02881.
authors.forename: Brenton
authors.initials: B
authors.lastname: DeBoef
keywords: Grignard reagent; amination; chloroamine; metal-free