Bis(NHC)-Pd-catalyzed one-pot competitive C–C*C–C, C–C*C–O, C–C*C–N, and C–O*C–N cross-coupling reactions on an aryl di-halide catalyzed by a homogenous basic ionic liquid (TAIm[OH]) under base-free, ligand-free, and solvent-free conditions. (16th June 2021)

• Record Type: Journal Article
• Authors: Zhu, Yanfang; Xu, Guiyang; Kazemnejadi, Milad
• Is Part Of: New journal of chemistry. Volume 45:Number 26(2021)
• Page Start: 11662
• Page End: 11671
• Publication Date: 2021-06-16
• Subjects: Chemistry -- Periodicals; Chimie -- Périodiques; 540
• DOI: 10.1039/d1nj00067e
• Languages: English
• ISSNs: 1144-0546

Abstract

Abstract : A new ionic liquid with intrinsic basic, ligand, and solvent properties is developed for efficient and selective Pd-catalyzed asymmetric C–C, C–O, and C–N cross-coupling reactions under mild conditions. Abstract : Bis(NHC)-Pd-catalyzed competitive asymmetrical C–C*C–C, C–C*C–O, C–C*C–N, and O–C*C–N cross-coupling reactions were performed via the one-pot strategy in the presence of a new ionic liquid, which played the roles of solvent, base, and ligand simultaneously. The ionic liquid was prepared based on a methyl imidazolium moiety with hydroxyl counter anions via a Hofmann elimination on a 1, 3, 5-triazine framework (TAIm[OH]). Pd ions could be efficiently coordinated through the bis(NHC)-ligand moiety in the ionic liquid. Based on differences in the competitive kinetics of C–C cross-coupling reactions (Heck, Suzuki, and Sonogashira) with C–N and C–O cross-coupling reactions, and also differences in the kinetics of aryl halides, the coupling reactions could be selectively performed with a low amount of by-products. The competitive cross-coupling reactions were thus performed with high selectivity under mild reaction conditions.