Electrophilic Aromatic Aroylation with CF₃‐Bearing Arenecarboxylic Acid Derivatives: Reaction Behavior and Acidic Mediator Dependence

References

• Kajiyama , M. , Kudo , J. and Mizumachi , H. 1999 . Synthesis and characterization of aromatic polymers derived from 5‐perfluoroalkylisophthalic acid . J. Polym. Sci., Part A: Polym. Chem. , 37 : 1135 – 1141 .
   Google Scholar
• Zhang , L. and Huang , W. 2000 . Synthesis of polyfluorinated aromatic polyesters . J. Fluorine Chem. , 102 : 55 – 59 .
   Google Scholar
• Chung , I. and Kim , S. 2001 . Meta‐activated nucleophilic aromatic substitution reaction: Poly(biphenylene oxide)s with trifluoromethyl pendant groups via nitro displacement . J. Am. Chem. Soc. , 123 : 11071 – 11072 .
   PubMed Web of Science ®Google Scholar
• Salunke , A. , Madhra , M. , Sharma , M. and Benerjee , S. 2002 . Synthesis and characterization of poly(arylene ether)s derived from 4,4′‐bishydroxybiphenyl and 4,4′‐bishydroxyterphenyl . J. Polym. Sci., Part A: Polym. Chem. , 40 : 55 – 69 .
   Web of Science ®Google Scholar
• Krafft , M. and Riess , J. 1998 . Highly fluorinated amphiphiles and colloidal systems, and their applications in the biochemical field. A contribution . Biochimie , 80 : 489 – 514 .
   PubMed Web of Science ®Google Scholar
• McBee , E. T. , Resconich , S. and Belohlav , L. R. 1963 . The reaction of ethylmagnesium bromide with acetophenones and trifluoroacetophenones . J. Org. Chem. , 28 : 3579 – 3580 .
   Google Scholar
• Huang , Y. and Qing , F. 2004 . Fluorous glycol derivatives: Novel carbonyl protective groups . Tetrahedron , 60 : 8341 – 8346 .
   Google Scholar
• Zhdankin , V. and Kuehl , C. 1994 . [Hydroxy(sulfonyloxy)iodo]perfluoroalkanes–New hypervalent iodine species and promising reagents for organic synthesis . Tetrahedron Lett. , 35 : 1809 – 1812 .
   Google Scholar
• Fuchigami , T. and Yamamoto , K. 1991 . Electrolytic reactions of fluoro organic compounds, 7: Anodic methoxylation and acetoxylation of 2,2,2‐trifluoroethyl sulfides: Preparation of highly useful trifluoromethylated building blocks . J. Org. Chem. , 56 : 137 – 142 .
   Google Scholar
• Arnold‐Stanton , R. and Lemal , D. M. 1991 . Fluorinated bifunctional derivatives of bisphenol A . J. Org. Chem. , 56 : 146 – 151 .
   Google Scholar
• Osawa , M. , Kusumoto , A. and Takehara , S. 2002 . Methylenecyclohexane derivative, liquid crystal composition containing it, and liquid crystal display device using the composition . Jpn. Kokai Tokkyo Koho , JP 2002220356
   Google Scholar
• Takiguchi , T. , Nakamura , S. and Sato , K. 2001 . Optically active aromatic compound, ferroelectric/antiferroelectric liquid crystal composition and liquid crystal device using it . Jpn. Kokai Tokkyo Koho , JP 2001089410
   Google Scholar
• Sinta , R. , Gaudiana , R. A. and Rogers , H. G. 1989 . Novel thermotropic poly(ester amides) . J. Macromol. Sci. Chem. , A26 : 773 – 785 .
   Google Scholar
• Kimura , T. , Duan , X. and Kato , M. 1998 . Synthesis and nonlinear optical properties of end‐group modified aromatic esters as chained chromophores . Macromol. Chem. Phys. , 199 : 1193 – 1199 .
   Google Scholar
• Pews , R. G. , Tsuno , Y. and Taft , R. W. 1967 . A fluorine nuclear magnetic resonance shielding study of substituent effects on π‐charge distributions in benzophenone and its Lewis acid adducts . J. Am. Chem. Soc. , 89 : 2391 – 2396 .
   Google Scholar
• Giam , C. S. and Taft , R. W. 1967 . Evaluation of ground‐state electronic energy from fluorine nuclear magnetic resonance shielding. I. Prediction of enthalpies of reaction for formation of Lewis acid adducts of benzophenones . J. Am. Chem. Soc. , 89 : 2397 – 2401 .
   Google Scholar
• Dayal , S. K. , Ehrenson , S. and Taft , R. W. 1972 . Substituent effects, electronic transmission and structural dependence of π delocalization as studied with the p‐fluorophenyl tag . J. Am. Chem. Soc. , 94 : 9113 – 9122 .
   Web of Science ®Google Scholar
• Trost , B. M. and Weber , L. 1975 . Regarding π‐electron transmission of substituent polar effects on fluorine nuclear magnetic resonance shielding . J. Am. Chem. Soc. , 97 : 1612 – 1615 .
   Google Scholar
• Yokozawa , T. , Suzuki , Y. and Hiraoka , S. 2001 . Aromatic polyethers with low polydispersities from chain‐growth polycondensation . J. Am. Chem. Soc. , 123 : 9902 – 9903 .
   PubMedGoogle Scholar
• Suzuki , Y. , Hiraoka , S. , Yokoyama , A. and Yokozawa , T. 2003 . Chain‐growth polycondensation for aromatic polyethers with low polydispersities: Living polymerization nature in polycondensation . Macromolecules , 36 : 4756 – 4765 .
   Google Scholar
• Suzuki , Y. , Hiraoka , S. , Yokoyama , A. and Yokozawa , T. 2004 . Solvent effect on chain‐growth polycondensation for aromatic polyethers . J. Polym. Sci., Part A: Polym. Chem. , 42 : 1198 – 1207 .
   Google Scholar
• Minamitani , T. and Mochizuki , C. 1993 . Electrophotographic developing apparatus having aromatic fluoride‐coated toner‐supplying member . Jpn. Kokai Tokkyo Koho , JP 05011499
   Google Scholar
• Yamaguchi , K. 1992 . One‐component electrophotographic developer . Jpn. Kokai Tokkyo Koho , JP 04063357
   PubMedGoogle Scholar
• Yamaguchi , K. and Kawase , H. 1991 . Toners for electrostatic image development comprising suspension polymerization particle treated with fluorobenzophenone derivative . Jpn. Kokai Tokkyo Koho , JP 03188465
   Google Scholar
• DoAmaral , J. R. , Blanz , E. J. Jr. and French , F. A. 1969 . Antimalarial activity of guanylhydrazone salts of aromatic ketones, 1: Primary search for active substituent patterns . J. Med. Chem. , 12 : 21 – 25 .
   PubMedGoogle Scholar
• Wang , T. S. T. and Fawwaz , R. A. 1985 . Synthesis of 4‐fluoro‐4′‐trifluoromethylbenzophenone guanylhydrazone hydrochloride labeled with carbon‐14 . J. Label. Compd. Radiopharm. , 22 : 405 – 409 .
   Google Scholar
• Moore , J. S. 1992 . Poly(aryl ketones) via palladium‐catalyzed cross‐coupling . Makromol. Chem., Rapid Commun. , 13 : 91 – 96 .
   Google Scholar
• Deeter , G. A. and Moore , J. S. 1993 . A new polymerization reaction for the synthesis of aromatic polyketones . Macromolecules , 26 : 2535 – 2541 .
   Google Scholar
• Yonezawa , N. , Kameda , A. , Jobashi , T. , Maruyama , S. and Maeyama , K. 2004 . Synthesis of sequential wholly aromatic polyketone composed of 2,2′‐dimethoxybiphenylene unit . Polym. J. , 36 : 345 – 351 .
   Google Scholar
• Maeyama , K. , Ohe , T. , Nakamura , H. and Yonezawa , N. 2003 . Synthesis of fully aromatic polyketones without ether linkages in the main chain: Nickel complex‐mediated aromatic coupling polymerization of bis(chlorobenzoylated) o‐terphenyls . Polym. J. , 35 : 1009 – 1015 .
   Google Scholar
• Yonezawa , N. , Namie , T. , Ikezaki , T. , Hino , T. , Nakamura , H. , Tokita , Y. and Katakai , R. 1996 . Synthesis of aromatic polyketones by using biphenylene monomers . React. Funct. Polym. , 30 : 261 – 268 .
   Web of Science ®Google Scholar
• Maeyama , K. , Tagata , Y. and Yonezawa , N. 2004 . 2,2′‐bis(4‐benzoylphenoxy)biphenyl: A novel efficient acyl‐acceptant monomer yielding wholly aromatic polyketones via Friedel–Crafts type polymerization with arenedicarbonyl chloride . Polym. J. , 36 : 146 – 150 .
   Google Scholar
• Yonezawa , N. , Mori , S. , Miyata , S. , Ueha‐Anyashiki , Y. , Wu , S. and Maeyama , K. 2003 . Electrophilic aromatic acylation synthesis of wholly aromatic polyketones composed of 2,2′‐dimethoxybiphenylene units . Polym. J. , 35 : 998 – 1002 .
   Google Scholar
• Yonezawa , N. , Ikezaki , T. , Nakamura , H. and Maeyama , K. 2000 . Successful synthesis of wholly aromatic polyketones via nickel‐mediated aromatic coupling polymerization . Macromolecules , 33 : 8125 – 8129 .
   Web of Science ®Google Scholar
• Eaton , P. E. and Carlson , G. R. 1973 . Phosphorus pentoxide–methanesulfonic acid: A convenient alternative to polyphosphoric acid . J. Org. Chem. , 38 : 4071 – 4073 .
   Web of Science ®Google Scholar
• Ridd , J. H. and Yousaf , T. I. 1988 . Polymerisation and related reactions involving nucleophilic aromatic substitution. Part 1: The rates of reaction of substituted 4‐halogenobenzophenones with the potassium salts of substituted 4‐hydroxybenzophenones . J. Chem. Soc., Perkin 2 , : 1729 – 1734 .
   Google Scholar
• Maeyama , K. , Ogura , K. , Okamoto , A. , Sakurai , K. , Yoshida , Y. , Ogino , K. and Yonezawa , N. 2004 . P2O5–MsOH mediated regioselective diaroylation of 2,2′‐dimethoxy‐1,1′‐binaphthyl . Synth. Commun. , 34 : 3243 – 3250 .
   Web of Science ®Google Scholar
• Fuchibe , K. and Akiyama , T. 2006 . Low‐valent niobium‐mediated double activation of C‐F/C‐H bonds: Fluorene synthesis from o‐arylated α,α,α‐trifluorotoluene derivatives . J. Am. Chem. Soc. , 128 : 1434 – 1435 .
   PubMedGoogle Scholar
• Olah , G. A. 1993 . Superelectrophilies . Angew. Chem. Int. Ed. Engl. , 32 : 767 – 788 .
   Google Scholar
• Zhong , J. , Wang , Y. and Deng , R. 1983 . Syntheses of antimalarial drugs, derivatives of substituted benzophenones . Yiyao Gongye , 8 : 10 – 12 . (in Chinese) Chem. Abstr., 1983, 100, 138714
   Google Scholar
• DoAmaral , J. R. , French , F. A. , Blanz , E. J. Jr. and French , D. A. 1971 . Antimalarial activity of guanylhydrazone salts of aromatic ketones, 2: Development of active polyhalo derivatives . J. Med. Chem. , 14 : 862 – 866 .
   PubMedGoogle Scholar