α-Arylation of Amides from α-Halo Amides Using Metal-Catalyzed Cross-Coupling Reactions

E. Barde; A. Guérinot; J. Cossy

doi:10.1055/s-0037-1611358

Synthesis, Table of Contents

CC BY ND NC 4.0 · Synthesis 2019; 51(01): 178-184
DOI: 10.1055/s-0037-1611358

short review

Copyright with the author

α-Arylation of Amides from α-Halo Amides Using Metal-Catalyzed Cross-Coupling Reactions

E. Barde

,

A. Guérinot *

Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI)-UMR 8231, ESPCI Paris, CNRS, PSL Research University, 10 rue Vauquelin, 75231 Paris Cedex 05, France Email: amandine.guerinot@espci.fr Email: janine.cossy@espci.fr

,

J. Cossy *

Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI)-UMR 8231, ESPCI Paris, CNRS, PSL Research University, 10 rue Vauquelin, 75231 Paris Cedex 05, France Email: amandine.guerinot@espci.fr Email: janine.cossy@espci.fr

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Abstract

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Published as part of the 50 Years SYNTHESIS – Golden Anniversary Issue

Abstract

Metal-catalyzed α-arylation of amides from α-halo amides with organometallic reagents is reviewed. The article includes Suzuki–Miyaura, Kumada–Corriu, Negishi, and Hiyama cross-coupling reactions.

1 Introduction

2 Suzuki–Miyaura Cross-Coupling

2.1 Palladium Catalysis

2.2 Nickel Catalysis

3 Kumada–Corriu Cross-Coupling

3.1 Nickel Catalysis

3.2 Iron Catalysis

3.3 Cobalt Catalysis

4 Negishi Cross-Coupling

5 Hiyama Cross-Coupling

6 Conclusion

Key words

amide - arylation - cross-coupling - metal catalysis

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References

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