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Issue 3, 2020
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Buchwald–Hartwig cross-coupling of amides (transamidation) by selective N–C(O) cleavage mediated by air- and moisture-stable [Pd(NHC)(allyl)Cl] precatalysts: catalyst evaluation and mechanism

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Abstract

The Pd–NHC-catalyzed acyl-type Buchwald–Hartwig cross-coupling of amides by N–C(O) cleavage (transamidation) provides a valuable alternative to the classical methods for amide synthesis. Herein, we report a combined experimental and computational study of the Buchwald–Hartwig cross-coupling of amides using well-defined, air- and moisture-stable [Pd(NHC)(allyl)Cl] precatalysts. Most crucially, we present a comprehensive evaluation of a series of distinct Pd(II)–NHC precatalysts featuring different NHC scaffolds and throw-away ligands for the synthesis of functionalized amides that are not compatible with stoichiometric transition-metal-free transamidation methods. Furthermore, we present evaluation of the catalytic cycle by DFT methods for a series of different Pd(II)–NHC precatalysts. The viability of accessing NHC-supported acyl-palladium(II) amido complexes will have implications for the design and development of cross-coupling methods involving stable amide electrophiles.

Graphical abstract: Buchwald–Hartwig cross-coupling of amides (transamidation) by selective N–C(O) cleavage mediated by air- and moisture-stable [Pd(NHC)(allyl)Cl] precatalysts: catalyst evaluation and mechanism

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Supplementary files

Article information


Submitted
15 Oct 2019
Accepted
20 Dec 2019
First published
23 Dec 2019

Catal. Sci. Technol., 2020,10, 710-716
Article type
Paper
Author version available

Buchwald–Hartwig cross-coupling of amides (transamidation) by selective N–C(O) cleavage mediated by air- and moisture-stable [Pd(NHC)(allyl)Cl] precatalysts: catalyst evaluation and mechanism

G. Li, T. Zhou, A. Poater, L. Cavallo, S. P. Nolan and M. Szostak, Catal. Sci. Technol., 2020, 10, 710 DOI: 10.1039/C9CY02080B

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