Bulky α-diimine palladium complexes: highly efficient for direct C–H bond arylation of heteroarenes under aerobic conditions. Issue 38 (18th August 2016)

• Record Type: Journal Article
• Authors: Ouyang, Jia-Sheng; Li, Yan-Fang; Shen, Dong-Sheng; Ke, Zhuofeng; Liu, Feng-Shou
• Is Part Of: Dalton transactions. Volume 45:Issue 38(2016)
• Page Start: 14919
• Page End: 14927
• Publication Date: 2016-08-18
• Subjects: Chemistry, Inorganic -- Periodicals; Chemistry, Physical and theoretical -- Periodicals; Chemistry, Inorganic -- Periodicals; 546.05
• DOI: 10.1039/c6dt02544g
• Languages: English
• ISSNs: 1477-9226

Abstract

Abstract : Through the strategy to enhance the bulkiness on both the backbone and the N -aryl moieties, we designed and synthesized a type of bulky α-diimine palladium complex ( i.e., {[Ar–NC(R)–C(R)N–Ar]PdCl2, (Ar = 2-benzhydryl-4, 6-dimethylphenyl)}, C1, R = H;C2, R = An;C3, R = Ph). Abstract : Through the strategy to enhance the bulkiness on both the backbone and the N -aryl moieties, we designed and synthesized a type of bulky α-diimine palladium complex ( i.e., {[Ar–NC(R)–C(R)N–Ar]PdCl2, (Ar = 2-benzhydryl-4, 6-dimethylphenyl)}, C1, R = H;C2, R = An;C3, R = Ph). The structures of these palladium complexes were well characterized, whileC1 andC3 were further characterized by X-ray diffraction. The catalytic performances of the precatalysts were screened for direct C–H bond arylation of heteroarenes. The bidentate N, N -palladium complexC3 with both a backbone and N -aryl bulkiness was found to be a highly efficient precatalyst under aerobic conditions. With a low palladium loading of 0.5–0.1 mol%, a variety of heteroarenes with challenging bulky steric aryl bromides as well as heteroaryl bromides are all applicable for this cross-coupling reaction.