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. 2006 Jun 13;103(24):8928-33.
doi: 10.1073/pnas.0601687103. Epub 2006 Jun 5.

Cu-catalyzed cross-dehydrogenative coupling: a versatile strategy for C-C bond formations via the oxidative activation of sp(3) C-H bonds

Zhiping Li  1 , D Scott Bohle, Chao-Jun Li
Affiliations

Cu-catalyzed cross-dehydrogenative coupling: a versatile strategy for C-C bond formations via the oxidative activation of sp(3) C-H bonds

Zhiping Li et al. Proc Natl Acad Sci U S A. .

Abstract

Cu-catalyzed cross-dehydrogenative coupling (CDC) methodologies were developed based on the oxidative activation of sp(3) C-H bonds adjacent to a nitrogen atom. Various sp, sp(2), and sp(3) C-H bonds of pronucleophiles were used in the Cu-catalyzed CDC reactions. Based on these results, the mechanisms of the CDC reactions also are discussed.

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Conflict of interest statement

Conflict of interest statement: Part of the research results will be filed for patent protection.

Figures

Scheme 1.
Scheme 1.
Various cross-coupling methods for the formation of C–C bonds.
Scheme 2.
Scheme 2.
Reaction of 1-phenylpyrrolidine with nitromethane.
Scheme 3.
Scheme 3.
CDC reaction of tetrahydroisoquinoline with Meldrum’s acid.
Scheme 4.
Scheme 4.
CDC reaction of tetrahydroisoquinoline with indole.
Scheme 5.
Scheme 5.
Various methods for forming propargylamines.
Scheme 6.
Scheme 6.
Reaction of N,N-dimethylbenzylamine with alkynes.
Scheme 7.
Scheme 7.
Reaction of cyclic benzylamine with alkynes.
Scheme 8.
Scheme 8.
Reaction of simple cyclic amine.
Scheme 9.
Scheme 9.
Radical mechanism for the CDC reaction of amine with nucleophile.
Scheme 10.
Scheme 10.
Ionic mechanism for the CDC reaction of amine with nucleophile.
Scheme 11.
Scheme 11.
CDC reaction of amine with nitromethane in the presence of 2,6-di-tert-butyl-4-methyl phenol (BHT).
See this image and copyright information in PMC

References

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