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Title: Copper‐Catalyzed Dehydrogenative Amidation of Light Alkanes

Journal Article · · Angewandte Chemie (International Edition)
ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [2]; ORCiD logo [2]; ORCiD logo [1]; ORCiD logo [2]; ORCiD logo [1]
  1. Laboratorio de Catálisis Homogénea Unidad Asociada al CSIC CIQSO-Centro de Investigación en Química Sostenible and Departamento de Química Universidad de Huelva 21007 Huelva Spain
  2. Department of Chemistry University of California Berkeley CA 94720 USA
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Abstract The functionalization of C−H bonds in light alkanes, particularly to form C−N bonds, remains a challenge. We report the dehydrogenative coupling of amides with C1–C4 hydrocarbons to form N‐alkyl amide products with tBuOOtBu as oxidant, and a copper complex of a phenanthroline‐type ligand as catalyst. The reactions occurred in good yields in benzene or supercritical carbon dioxide as solvents. This strategy allowed for the determination of the relative reactivity of these alkane C−H bonds toward this amination process and showed, in contrast to prior work with larger alkanes, that the reactivity correlated with bond dissociation energies.

Research Organization:
Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)
Sponsoring Organization:
USDOE; USDOE Office of Science (SC)
Grant/Contract Number:
AC02-05CH11231
OSTI ID:
1808332
Journal Information:
Angewandte Chemie (International Edition), Journal Name: Angewandte Chemie (International Edition) Journal Issue: 34 Vol. 60; ISSN 1433-7851
Publisher:
Wiley Blackwell (John Wiley & Sons)Copyright Statement
Country of Publication:
Germany
Language:
English

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
C−H bond activation
C−N bond formation
copper catalysis
dehydrogenative alkane functionalization
light alkane amidation