934008-48-7Relevant articles and documents
Cu(I)–N-heterocyclic carbene-catalyzed base free C–N bond formation of arylboronic acids with amines and azoles
Zhang, Maoyuan,Xu, Zengbing,Shi, Dabin
, (2020/12/25)
A new N-heterocyclic carbene (NHC) precursor of imidazolium chloride and its corresponding Cu(I)–NHC complex 1 was synthesized. The complex 1 was found to be a highly effective catalyst for Chan-Evans-Lam coupling of arylboronic acid with amines and azoles (including imidazole, pyrazole and triazole), without addition of base at room temperature. Various substituents on three substrates can be tolerated, giving the desired coupling products in good to excellent yields (62–94%). The method is practical and offers an alternative to the corresponding copper-catalyzed Chan-Evans-Lam process for the construction of C–N bonds.
Synthesis of Pd Complexes Containing Tailed NHC Ligands and Their Use in a Semicontinuous Membrane-Assisted Suzuki Cross-Coupling Process
Ormerod, Dominic,Dorbec, Matthieu,Merkul, Eugen,Kaval, Nadya,Lefèvre, Nicolas,Hostyn, Steven,Eykens, Lies,Lievens, Jo,Sergeyev, Sergey,Maes, Bert U. W.
, p. 1509 - 1517 (2018/10/25)
Homogeneous catalysis has proved to be a reliable method for preparing numerous molecular entities, but catalysts can be expensive and difficult to remove. Because of this, industry targets catalysts that are easily separated and recovered and feature increased turnover numbers. The ongoing shift from multipurpose batch reactors toward continuous manufacturing in fine chemicals synthesis results in a new set of catalyst requirements. This paper reports the design and use of Pd complexes suitable for a semicontinuous Suzuki cross-coupling reaction based on a membrane-assisted reactor. These Pd complexes contain tailed N-heterocyclic carbene (NHC) ligands, allowing internal catalyst recovery by organic solvent nanofiltration with top-layer-modified ceramic membranes. These membranes give selective nanofiltration of the catalyst based on a combination of size exclusion and affinity separation (solvent-solute-membrane interactions). The semicontinuous system developed led to significantly improved turnover numbers, simplified product isolation, and consequently reduced mass intensity by simply adding more of the reactants and reagents to the reaction vessel.
Synthesis and catalytic application of: N -heterocyclic carbene copper complex functionalized conjugated microporous polymer
Zhou, Hui,Zhang, Qing-Yong,Lu, Xiao-Bing
, p. 44995 - 45000 (2016/06/06)
A N-heterocyclic carbene copper(i) complex functionalized conjugated microporous polymer (CMP-NHC-CuCl) was synthesized by palladium-catalyzed Sonogashira cross-coupling chemistry. The resulting CMP-NHC-CuCl proved to be a good heterogeneous catalyst in the hydrosilylation of functionalized terminal alkynes with boryldisiloxane to afford (β,β)-(E)-vinyldisiloxane with high stereoselectivity, and the catalyst could be used four times without obvious loss in catalytic activity. Moreover, CMP-NHC-CuCl was also efficient in catalyzing the hydrosilylation of CO2 with triethoxysilane to form silyl formate under mild conditions.
