N‑Heterocyclic Carbene–Palladium(II)–1-Methylimidazole Complex-Catalyzed Suzuki–Miyaura Coupling of Aryl Sulfonates with Arylboronic Acids

• Published in: Journal of organic chemistry 2012-08, Vol.77 (15), p.6608-6614
• Main Authors: Wang, Zhan-Yong, Chen, Gao-Qi, Shao, Li-Xiong
• Format: Article
• Language: English
• Subjects: Arylsulfonates - chemistry; B derivatives; Biphenyl Compounds - chemical synthesis; Biphenyl Compounds - chemistry; Boronic Acids - chemistry; Catalysis; Catalysts: preparations and properties; Chemistry; Exact sciences and technology; General and physical chemistry; Heterocyclic compounds; Heterocyclic Compounds - chemistry; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Imidazoles - chemistry; Methane - analogs & derivatives; Methane - chemistry; Molecular Structure; Noncondensed benzenic compounds; Organic chemistry; Organometallic Compounds - chemistry; Organometalloidal and organometallic compounds; Palladium - chemistry; Preparations and properties; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo301270t

A well-defined NHC–Pd(II)–Im complex 1 was found to be an effective catalyst for the Suzuki–Miyaura coupling of aryl sulfonates including tosylates and phenylsulfonates with arylboronic acids, giving the desired coupling products in good to high yields. Acceptable yields can also be achieved even by using the less reactive mesylates as the substrates. It is worthy of noting here that this is the first example of NHC–Pd(II) complex-catalyzed Suzuki–Miyaura coupling of aryl sulfonates with arylboronic acids, enriching an inexpensive, convenient, and alternative method for the synthesis of biaryl compounds.