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Chem Commun (Camb). 2019 Aug 7;55(61):9003-9006. doi: 10.1039/c9cc04072b. Epub 2019 Jul 10.

Ruthenium(0)-sequential catalysis for the synthesis of sterically hindered amines by C-H arylation/hydrosilylation.

Author information

1
Department of Chemistry, Rutgers University, 73 Warren Street, Newark, NJ 07102, USA. michal.szostak@rutgers.edu.
2
College of Chemistry and Chemical Engineering and Key Laboratory of Auxiliary Chemistry and Technology for Chemical Industry, Ministry of Education, Shaanxi University of Science and Technology, Xi'an 710021, China and Department of Chemistry, Rutgers University, 73 Warren Street, Newark, NJ 07102, USA. michal.szostak@rutgers.edu.

Abstract

We report sequential ruthenium(0)-catalysis for the synthesis of sterically-hindered amines via direct C-H arylation of simple imines and imine hydrosilylation. The method involves direct C-H arylation under neutral conditions with organoboranes enabled by ruthenium(0) catalysis. The catalytic hydrosilylation was performed in a one-pot fashion using Et3SiH. The reaction is compatible with a broad range of electronically- and sterically-varied imines, enabling rapid production of valuable biaryl amines in good to excellent yields. The method constitutes a two-step, one-pot procedure to synthesize sterically-hindered amines from aldehydes. The utility of this atom-economic strategy is demonstrated in one-pot, three-component coupling, direct in situ aldehyde arylation and the use of transfer hydrogenation.

PMID:
31290865
DOI:
10.1039/c9cc04072b

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