NHC–Pd(II)–Im (NHC = N-heterocyclic carbene; Im = 1-methylimidazole) complexes as efficient catalysts for Suzuki-Miyaura coupling reactions of aryl chlorides

A new type of well-defined N-heterocyclic carbene (NHC)-palladium chloride-imidazole complexes derived from IPrHCl or IMesHCl, PdCl2 and 1-methylimidazole exhibits high catalytic activity in the room-temperature Suzuki-Miyaura coupling reactions of aryl or heteroaryl chlorides. Moreover, the large-scale (20.0 mmol) couplings in the presence of 0.01 mol% catalyst loading can also give the corresponding coupling products in high yields.

Graphical abstractWell-defined NHC-PdCl2-imidazole complexes derived from IPrHCl or IMesHCl, PdCl2 and 1-methylimidazole exhibit high catalytic activity in the Suzuki-Miyaura coupling of aryl or heteroaryl chlorides. Moreover, the large-scale couplings in the presence of 0.01 mol% catalyst loading can also give the corresponding products in high yields.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► NHC–Pd(II)–Im complexes showed high activity in Suzuki coupling of aryl chlorides. ► The large-scale couplings can also give the coupling products in high yields. ► Large-scale couplings make the reactions suitable toward an industrial level.