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Communication

Suzuki–Miyaura Cross-Coupling of Amides Using Well-Defined, Air- and Moisture-Stable Nickel/NHC (NHC = N-Heterocyclic Carbene) Complexes

Department of Chemistry, Rutgers University, 73 Warren Street, Newark, NJ 07102, USA
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Author to whom correspondence should be addressed.
Catalysts 2020, 10(4), 372; https://doi.org/10.3390/catal10040372
Received: 6 March 2020 / Revised: 24 March 2020 / Accepted: 25 March 2020 / Published: 31 March 2020
(This article belongs to the Special Issue N‐Heterocyclic Carbenes and Their Complexes in Catalysis)
In this Special Issue on N-Heterocyclic Carbenes and Their Complexes in Catalysis, we report the first example of Suzuki–Miyaura cross-coupling of amides catalyzed by well-defined, air- and moisture-stable nickel/NHC (NHC = N-heterocyclic carbene) complexes. The selective amide bond N–C(O) activation is achieved by half-sandwich, cyclopentadienyl [CpNi(NHC)Cl] complexes. The following order of reactivity of NHC ligands has been found: IPr > IMes > IPaul ≈ IPr*. Both the neutral and the cationic complexes are efficient catalysts for the Suzuki–Miyaura cross-coupling of amides. Kinetic studies demonstrate that the reactions are complete in < 1 h at 80 °C. Complete selectivity for the cleavage of exocyclic N-acyl bond has been observed under the experimental conditions. Given the utility of nickel catalysis in activating unreactive bonds, we believe that well-defined and bench-stable [CpNi(NHC)Cl] complexes will find broad application in amide bond and related cross-couplings of bench-stable acyl-electrophiles. View Full-Text
Keywords: N-heterocyclic carbenes; nickel; nickel/NHC; amide bonds; Suzuki–Miyaura; cross-coupling; N–C cleavage; N–C activation; [CpNi(NHC)X]; half-sandwich; cyclopentadienyl N-heterocyclic carbenes; nickel; nickel/NHC; amide bonds; Suzuki–Miyaura; cross-coupling; N–C cleavage; N–C activation; [CpNi(NHC)X]; half-sandwich; cyclopentadienyl
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MDPI and ACS Style

Buchspies, J.; Rahman, M.M.; Szostak, M. Suzuki–Miyaura Cross-Coupling of Amides Using Well-Defined, Air- and Moisture-Stable Nickel/NHC (NHC = N-Heterocyclic Carbene) Complexes. Catalysts 2020, 10, 372. https://doi.org/10.3390/catal10040372

AMA Style

Buchspies J, Rahman MM, Szostak M. Suzuki–Miyaura Cross-Coupling of Amides Using Well-Defined, Air- and Moisture-Stable Nickel/NHC (NHC = N-Heterocyclic Carbene) Complexes. Catalysts. 2020; 10(4):372. https://doi.org/10.3390/catal10040372

Chicago/Turabian Style

Buchspies, Jonathan, Md. M. Rahman, and Michal Szostak. 2020. "Suzuki–Miyaura Cross-Coupling of Amides Using Well-Defined, Air- and Moisture-Stable Nickel/NHC (NHC = N-Heterocyclic Carbene) Complexes" Catalysts 10, no. 4: 372. https://doi.org/10.3390/catal10040372

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