21.1.8 Synthesis of Amides by Transamidation and Amidation of Activated Amides and Esters

G. Li; M. Szostak

doi:10.1055/sos-SD-121-00059

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Christmann, M. et al.: 2020 Science of Synthesis, 2020/2: Knowledge Updates 2020/2 DOI: 10.1055/sos-SD-121-00059

Knowledge Updates 2020/2

21.1.8 Synthesis of Amides by Transamidation and Amidation of Activated Amides and Esters

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Editors: Christmann, M.; Huang, Z.; Joule, J. A.; Li, C.-J.; Li, J. J.; Marschner, C.; Petersson, E. J.; Reissig, H.-U.; Terent'ev, A. O.

Authors: Ambhaikar, N. B.; Campagne, J. M.; Celik, I. E.; Dembitsky, V. M.; Graham, M. A.; Holzschneider, K.; Jaschinski, M.; Kipke, W.; Kirsch, S. F.; Kunz, K.; Leclerc, E.; Li, G.; Li, Z.; Makow, J.; Müller, T.; Ochoa, C. I.; Ramirez y Medina, I.-M.; Rayner, C. M.; Staubitz, A.; Sun, X.-L.; Szostak, M.; Tambar, U. K.; Tian, T.; Tong, M. L.; Wang, X.-Y.; Yaremenko, I. A.; Yoshikai, N.

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. A.; Nevado, C.; Trost, B. M.; You, S.-L.

Type: Multivolume Edition

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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

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