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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.

SUBMITTER: Sirois JJ

PROVIDER: S-EPMC4604600 | biostudies-literature | 2015 Oct

REPOSITORIES: biostudies-literature

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Transition-metal free umpolung carbon-nitrogen vs. carbon-chlorine bond formation.

Sirois John J JJ DeBoef Brenton B

Tetrahedron letters 20151001 41

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. ...[more]

PMID: 26478603

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