Zirconocene Bis(perfluorooctanesulfonate)s-Catalyzed Highly Efficient Synthesis of 1,3,5-Triaryl Benzene via Cyclotrimerization of Ketones

REFERENCES

• Scott , L. T. ; In Modern Arene Chemistry ; D. Astruc (Ed.); Wiley : Berlin , 2002 ; pp. 20 – 31 .
   Google Scholar
• Kumar , A. ; Dixit , M. ; Singh , S. P. ; Raghunandan , R. ; Maulik , R. R. ; Goel , A. Reusable resin amberlyst 15 catalyzed new convenient protocol for accessing arylated benzene scaffolds . Tetrahedron Lett. 2009 , 50 , 4335 – 4339 .
   Web of Science ®Google Scholar
• Amick , A. W. ; Scott , L. T. Trisannulated benzene derivatives by acid-catalyzed aldol cyclotrimerizations of cyclic ketones: Methodology development and mechanistic insight . J. Org. Chem. 2007 , 72 , 3412 – 3418 .
   PubMed Web of Science ®Google Scholar
• Cao , X.-Y. ; Liu , X.-H. ; Zhou , X.-H. ; Zhang , Y. ; Jiang , Y. ; Cao , Y. ; Cui , Y.-X. ; Pe , J. Giant extended π-conjugated dendrimers containing the 10,15-dihydro-5H-diindeno[1,2-a;1′,2′-c]fluorene chromophore: Synthesis, NMR behaviors, optical properties, and electroluminescence. J. Org. Chem. 2004, 69, 6050–6058.
   PubMed Web of Science ®Google Scholar
• Elamparuthi , E. ; Ramesh , E. ; Raghunathan , R. InCl3 as an efficient catalyst for cyclotrimerization of aldehydes: Synthesis of 1,3,5-trioxane under solvent-free conditions . Synth. Commun. 2005 , 35 , 2801 – 2804 .
   Web of Science ®Google Scholar
• Aly , A. A. Triple self-condensation of fused cycloalkanonylparacyclophanes promoted by titanium tetrachloride and triethylamine . Tetrahedron Lett. 2005 , 46 , 443 – 446 .
   Web of Science ®Google Scholar
• Suzuki , K. ; Hintermann , L. ; Yamanoi , S. Cationic zirconocene species in organic synthesis . In Titanium and Zirconium in Organic Synthesis ; I. Marek (Ed.); Wiley-VCH : Weiheim , Germany , 2002 ; pp. 282 – 285 .
   Google Scholar
• Kottawar , S. ; Siddiqui , S. ; Chavan , V. ; Jadhav , W. ; Bhusare , S. Scandium(III) triflate–catalyzed efficient synthesis of substituted 1-pyridylimidazo-[1,5-a]-pyridines . Synth. Commun. 2009 , 29 , 3546 – 3549 .
   Web of Science ®Google Scholar
• Lasser , W. ; Thewalt , U. Darstellung und struktur zweier salze mit dem bis(μ-hydroxo)-bis(triaqua-π-cyclopentadienyl-zirkonium(IV)-kation . J. Organomet. Chem. 1986 , 311 , 69 – 77 .
   Web of Science ®Google Scholar
• Hollis , T. K. ; Robison , N. P. ; Bosnich , B. Homogeneous catalysis. [TiCp2(CF3SO3)2] and [ZrCp2(CF3SO3)2THF], fast and efficient catalysts for the Mukaiyama cross-aldol reaction . Tetrahedron Lett. 1992 , 33 , 6423 – 6426 .
   Web of Science ®Google Scholar
• Hollis , T. K. ; Bosnich , B. Homogeneous catalysis. Mechanisms of the catalytic mukaiyama aldol and sakurai allylation reactions . J. Am. Chem. Soc. 1995 , 117 , 4570 – 4581 .
   Web of Science ®Google Scholar
• Luinstra , G. A. Synthesis and reactivity of titanocene and zirconocene triflates . J. Organomet. Chem. 1996 , 517 , 209 – 215 .
   Web of Science ®Google Scholar
• An , D. ; Peng , Z. ; Orita , A. ; Kurita , A. ; Mane , S. ; Ohkubo , K. ; Li , X. ; Fukuzumi , S. ; Otera , J. Organotin perfluorooctanesulfonates as air-stable Lewis acid catalysts : Synthesis, characterization, and catalysis . Chem.-Eur. J. 2006 , 12 , 1642 – 1647 .
   PubMed Web of Science ®Google Scholar
• Qiu , R. ; Zhang , G. ; Zhu , Y. ; Xu , X. ; Shao , L. ; Li , Y. ; An , D. ; Yin , S. Synthesis and structure of an extremely air-stable binuclear hafnocene perfluorooctanesulfonate complex and its use in lewis acid–catalyzed reactions . Chem.-Eur. J. 2009 , 15 , 6488 – 6454 .
   PubMed Web of Science ®Google Scholar
• Qiu , R. ; Xu , X. ; Li , Y. ; Zhang , G. ; Shao , L. ; An , D. ; Yin , S. Synthesis and structure of air-stable Lewis acidic binuclear complex of zirconocene pentafluorophenylsulfonate and its catalytic application in the allylation of carbonyl compounds with tetraallyltin . Chem. Commun. 2009 , 1679 – 1681 .
   PubMed Web of Science ®Google Scholar
• Qiu , R. ; Zhang , G. ; Xu , X. ; Zou , K. ; Shao , L. ; Fang , D. ; Li , Y. ; Orita , A. ; Saijo , R. ; Mineyama , H. ; Suenobu , T. ; Fukuzumi , S. ; An , D. ; Otera , J. Metallocene bis(perfluoroalkanesulfonate)s as air-stable cationic lewis acids . J. Organomet. Chem. 2009 , 694 , 1524 – 1528 .
   Web of Science ®Google Scholar
• Qiu , R. ; Zhu , Y. ; Xu , X. ; Li , Y. ; Shao , L. ; Ren , X. ; Cai , X. ; An , D. ; Yin , S. Zirconocene bis(perfluorooctanesulfonate)s-catalyzed acylation of alcohols, phenols, thiols, and amines under solvent-free conditions . Catal. Commun. 2009 , 10 , 1889 – 1892 .
   Web of Science ®Google Scholar
• Ohkubo , K. ; Manson , S. C. ; Orita , A. ; Otera , J. ; Fukuzumi , S. Quantitative evaluation of lewis acidity of metal ions with different ligands and counterions in relation to the promoting effects of lewis acids on electron transfer reduction of oxygen . J. Org. Chem. 2003 , 68 , 4720 – 4726 .
   PubMed Web of Science ®Google Scholar
• Fukuzumi , S. ; Ohkubo , K. Fluorescence maxima of 10-methylacridone−metal ion salt complexes: A convenient and quantitative measure of lewis acidity of metal ion salts . J. Am. Chem. Soc. 2002 , 124 , 10270 – 10271 .
   PubMed Web of Science ®Google Scholar
• Jing , X. Xu , F. ; Zhu , Q. ; Ren , X. ; Yan , Ch. ; Wang , L. ; Wan , J. Novel method for the synthesis of 1,3,5-triarylbenzenes from ketones . Synth. Commun. 2005 , 35 , 3167 – 3171 .
   Web of Science ®Google Scholar