21.1. 8 Synthesis of Amides by Transamidation and Amidation of Activated Amides and Esters
Book
Editors: Christmann, M.; Huang, Z.; Joule, J. A.; Li, C.-J.; Li, J.; Marschner, C.; Petersson, E. J.; Reißig, H.-U.; Schaumann, E.; Terent'ev, A.
Title: Knowledge Updates 2020/2
Print ISBN: 9783132435612; Online ISBN: 9783132435636; Book DOI: 10.1055/b000000103
1st edition © 2020 Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart
Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry
Science of Synthesis Knowledge Updates
Parent publication
Title: Science of Synthesis
DOI: 10.1055/b-00000101
Series Editors: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G.; Nevado, C.; Trost, B. M.; You, S.
Type: Multivolume Edition
Abstract
This chapter provides a summary of the recent advances in direct transamidation and amidation reactions of activated amides and esters via transition-metal-catalyzed and transition-metal-free C(acyl)-N and C(acyl)-O bond cleavage as a new disconnection for the synthesis of amide bonds.
Key words
amides - esters - transamidation - amidation - N-C cleavage - O-C cleavage - tetrahedral intermediates - nucleophilic addition - cross coupling - palladium—NHC catalysis - nickel catalysis - nitroarenes - anilines - chemoselectivity - reductive coupling - twisted amides - ground-state destabilization - electronic activation- 3 Greenberg, A., Breneman, C. M., Liebman, J. F.. The Amide Linkage: Structural Significance in Chemistry, Biochemistry and Materials Science. Wiley-VCH; New York 2003
- 5 Bryan, M. C., Dunn, P. J., Entwistle, D., Gallou, F., Koenig, S. G., Hayler, J. D., Hickey, M. R., Hughes, S., Kopach, M. E., Moine, G., Richardson, P., Roschangar, F., Steven, A., Weiberth, F. J.. Green Chem.. 2018; 20: 5082
- 15 Li, G., Lei, P., Szostak, M., Casals-Cruañas, E., Poater, A., Cavallo, L., Nolan, S. P.. ChemCatChem. 2018; 10: 3096
- 22 Baker, E. L., Yamano, M. M., Zhou, Y., Anthony, S. M., Garg, N. K.. Nat. Commun.. 2016; 7: 11 554
- 25 Li, G., Zhou, T., Poater, A., Cavallo, L., Nolan, S. P., Szostak, M.. Catal. Sci. Technol.. 2020; 10
- 33 Gui, J., Pan, C.-M., Jin, Y., Qin, T., Lo, J. C., Lee, B. J., Spergel, S. H., Mertzman, M. E., Pitts, W. J., La Cruz, T. E., Schmidt, M. A., Darvatkar, N., Natarajan, S. R., Baran, P. S.. Science (Washington, D. C.). 2015; 348: 886
- 36 Hie, L., Nathel, N. F. F., Hong, X., Yang, Y.-F., Houk, K. N., Garg, N. K.. Angew. Chem. Int. Ed.. 2016; 55: 2810
- 40 Dardir, A. H., Melvin, P. R., Davis, R. M., Hazari, N., Beromi, M. M.. J. Org. Chem.. 2018; 83: 469