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Ni-Catalyzed Carbon-Carbon Bond-Forming Reductive Amination

Christoph Heinz, J. Patrick Lutz, Eric M. Simmons, Michael M. Miller, William R. Ewing and Abigail G. Doyle*

*Department of Chemistry, Princeton University, Princeton, New Jersey 08544, United States, Email: agdoyleprinceton.edu

C. Heinz, J. P. Lutz, E. M. Simmons, M. M. Miller, W. R. Ewing, A. G. Doyle, J. Am. Chem. Soc., 2018, 140, 2292-2300.

DOI: 10.1021/jacs.7b12212 (free Supporting Information)



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Abstract

A three-component, Ni-catalyzed reductive coupling enables a convergent synthesis of tertiary benzhydryl amines, which are challenging to access by traditional reductive amination methodologies. The condensation of secondary N-trimethylsilyl amines with benzaldehydes provides iminium ions in situ, which react with several distinct classes of organic electrophiles.

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Mechanistic investigations support a sequential oxidative addition mechanism rather than a pathway proceeding via α-amino radical formation.



Key Words

benzylamines, multicomponent reactions, zinc


ID: J48-Y2018