Bisimino-functionalized dibenzo[a,c]acridines as highly conjugated pincer frameworks for palladium(II): synthesis, characterization and catalytic performance in Heck coupling

	Bisimino-functionalized dibenzo[a,c]acridines as highly conjugated pincer frameworks for palladium(II): synthesis, characterization and catalytic performance in Heck coupling
	Mahmood, Qaiser 1,2,5; Yue, Erlin 1,2; Zhang, Wenjuan 1,2,3; Solan, Gregory A.1,2,4; Liang, Tongling 1,2; Sun, Wen-Hua1,2,5
刊名	ORGANIC CHEMISTRY FRONTIERS
	2016
卷号	3 期号:12 页码:1668-1679
英文摘要	A new pair of highly conjugated ligands, 10-[1-(arylimino)ethyl]-14-[(arylimino)methyl]dibenzo[a,c]acridine (aryl = 2,6-Me2Ph L1, 2,6-Et2Ph L2) incorporating both aldimine and ketimine units, have been prepared by a straightforward sequence of organic transformations from phenanthrene-9,10-dione. Cyclopalladation occurs readily at ambient temperature on treating L1 or L2 with PdCl2(NCCH3)(2) in aprotic solvents to afford exclusively (NketimineNC)Pd(II) chloride pincer complexes Pd1 or Pd2, respectively. By contrast in methanol, Pd1 or Pd2 are isolated as the minor product with aldehyde-containing Pd3 or Pd4 as the major one, the result of hydrolysis of the pendant aldimine units in Pd1 and Pd2, respectively. All the ligands and palladium complexes have been characterized by FT-IR, H-1 and C-13 NMR spectroscopy, mass spectrometry and elemental analysis; the molecular structures for L1, Pd1, Pd2, Pd3 and Pd4 are also reported. Using low catalyst loadings (0.0005-0.002 mol%) and elevated temperatures (140-200 degrees C), Pd1-Pd4 are able to efficiently mediate the coupling of haloarenes with vinyl-containing substrates with turnover numbers as high as 174 000; the effects of steric/electronic variation within the substrate and NNC-pincer complex on catalyst performance are examined.
收录类别	SCI
语种	英语
内容类型	期刊论文
源URL	[http://ir.iccas.ac.cn/handle/121111/36438]
专题	化学研究所_工程塑料实验室
作者单位	1.Chinese Acad Sci, Key Lab Engn Plast, Inst Chem, Beijing 100190, Peoples R China 2.Chinese Acad Sci, Beijing Natl Lab Mol Sci, Inst Chem, Beijing 100190, Peoples R China 3.Beijing Inst Fash Technol, Sch Mat Sci & Engn, Beijing 100029, Peoples R China 4.Univ Leicester, Dept Chem, Univ Rd, Leicester LE1 7RH, Leics, England 5.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
推荐引用方式 GB/T 7714	Mahmood, Qaiser,Yue, Erlin,Zhang, Wenjuan,et al. Bisimino-functionalized dibenzo[a,c]acridines as highly conjugated pincer frameworks for palladium(II): synthesis, characterization and catalytic performance in Heck coupling[J]. ORGANIC CHEMISTRY FRONTIERS,2016,3(12):1668-1679.
APA	Mahmood, Qaiser,Yue, Erlin,Zhang, Wenjuan,Solan, Gregory A.,Liang, Tongling,&Sun, Wen-Hua.(2016).Bisimino-functionalized dibenzo[a,c]acridines as highly conjugated pincer frameworks for palladium(II): synthesis, characterization and catalytic performance in Heck coupling.ORGANIC CHEMISTRY FRONTIERS,3(12),1668-1679.
MLA	Mahmood, Qaiser,et al."Bisimino-functionalized dibenzo[a,c]acridines as highly conjugated pincer frameworks for palladium(II): synthesis, characterization and catalytic performance in Heck coupling".ORGANIC CHEMISTRY FRONTIERS 3.12(2016):1668-1679.