The formation of carbon-nitrogen (C-N) bonds via an umpolung substitution reaction has been achieved at -78 degrees 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. (C) 2015 Elsevier Ltd. All rights reserved.
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Univ Toronto, Dept Chem, Davenport Res Labs, 80 St George St, Toronto, ON M5S 3H6, CanadaUniv Toronto, Dept Chem, Davenport Res Labs, 80 St George St, Toronto, ON M5S 3H6, Canada
Arora, Ramon
Samokhin, Philip
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Univ Toronto, Dept Chem, Davenport Res Labs, 80 St George St, Toronto, ON M5S 3H6, CanadaUniv Toronto, Dept Chem, Davenport Res Labs, 80 St George St, Toronto, ON M5S 3H6, Canada
Samokhin, Philip
Lautens, Mark
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Univ Toronto, Dept Chem, Davenport Res Labs, 80 St George St, Toronto, ON M5S 3H6, CanadaUniv Toronto, Dept Chem, Davenport Res Labs, 80 St George St, Toronto, ON M5S 3H6, Canada
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Department of Chemistry and Biochemistry, Ludwig-Maximilian University of Munich, 81377 MunichDepartment of Chemistry and Biochemistry, Ludwig-Maximilian University of Munich, 81377 Munich
Göbel M.
Tchitchanov B.H.
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Department of Chemistry and Biochemistry, Ludwig-Maximilian University of Munich, 81377 MunichDepartment of Chemistry and Biochemistry, Ludwig-Maximilian University of Munich, 81377 Munich
Tchitchanov B.H.
Murray J.S.
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Department of Chemistry, University of New Orleans, New Orleans
Department of Chemistry, Cleveland State University, ClevelandDepartment of Chemistry and Biochemistry, Ludwig-Maximilian University of Munich, 81377 Munich
Murray J.S.
Politzer P.
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Department of Chemistry, University of New Orleans, New Orleans
Department of Chemistry, Cleveland State University, ClevelandDepartment of Chemistry and Biochemistry, Ludwig-Maximilian University of Munich, 81377 Munich
Politzer P.
Klapötke T.M.
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Department of Chemistry and Biochemistry, Ludwig-Maximilian University of Munich, 81377 Munich
CECD, Departments of Mechanical Engineering and Chemistry/Biochemistry, University of Maryland, College ParkDepartment of Chemistry and Biochemistry, Ludwig-Maximilian University of Munich, 81377 Munich