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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

(2020) CATALYSIS SCIENCE & TECHNOLOGY. 10(3). p.710-716
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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.
Keywords
Catalysis, HETEROCYCLIC CARBENE COMPLEXES, (NHC)PD(ALLYL)CL NHC, SUZUKI-MIYAURA, BOND FORMATION, SECONDARY AMIDES, AMIDATION, AMINATION, REAGENTS, ESTERS

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MLA
Li, Guangchen, et al. “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.” CATALYSIS SCIENCE & TECHNOLOGY, vol. 10, no. 3, 2020, pp. 710–16, doi:10.1039/c9cy02080b.
APA
Li, G., Zhou, T., Poater, A., Cavallo, L., Nolan, S., & Szostak, M. (2020). 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. CATALYSIS SCIENCE & TECHNOLOGY, 10(3), 710–716. https://doi.org/10.1039/c9cy02080b
Chicago author-date
Li, Guangchen, Tongliang Zhou, Albert Poater, Luigi Cavallo, Steven Nolan, and Michal Szostak. 2020. “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.” CATALYSIS SCIENCE & TECHNOLOGY 10 (3): 710–16. https://doi.org/10.1039/c9cy02080b.
Chicago author-date (all authors)
Li, Guangchen, Tongliang Zhou, Albert Poater, Luigi Cavallo, Steven Nolan, and Michal Szostak. 2020. “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.” CATALYSIS SCIENCE & TECHNOLOGY 10 (3): 710–716. doi:10.1039/c9cy02080b.
Vancouver
1.
Li G, Zhou T, Poater A, Cavallo L, Nolan S, Szostak M. 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. CATALYSIS SCIENCE & TECHNOLOGY. 2020;10(3):710–6.
IEEE
[1]
G. Li, T. Zhou, A. Poater, L. Cavallo, S. Nolan, and M. Szostak, “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,” CATALYSIS SCIENCE & TECHNOLOGY, vol. 10, no. 3, pp. 710–716, 2020.
@article{8661461,
  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.},
  author       = {Li, Guangchen and Zhou, Tongliang and Poater, Albert and Cavallo, Luigi and Nolan, Steven and Szostak, Michal},
  issn         = {2044-4753},
  journal      = {CATALYSIS SCIENCE & TECHNOLOGY},
  keywords     = {Catalysis,HETEROCYCLIC CARBENE COMPLEXES,(NHC)PD(ALLYL)CL NHC,SUZUKI-MIYAURA,BOND FORMATION,SECONDARY AMIDES,AMIDATION,AMINATION,REAGENTS,ESTERS},
  language     = {eng},
  number       = {3},
  pages        = {710--716},
  title        = {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},
  url          = {http://dx.doi.org/10.1039/c9cy02080b},
  volume       = {10},
  year         = {2020},
}

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