Acylation reactions under microwaves. 3. Aroylation of benzene and its slightly activated or deactivated derivatives

Industrial and Engineering Chemistry Research

Volumn 39, Issue 5, 2000, Pages 1124-1131

  Marquié, Julien ^a   Laporte, Christian ^a   Laporterie, André ^a   Dubac, Jacques ^a   Desmurs, Jean Roger ^b   Roques, Nicolas ^b  

^a UNIVERSITÉ DE TOULOUSE   (France)

^b Rhodia Europe   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; DERIVATIVES; IRON COMPOUNDS; IRRADIATION; KETONES; METALLIC COMPOUNDS; MICROWAVES; NAPHTHALENE; REACTION KINETICS; TOLUENE; XYLENE;

AROYLATION; ARYL KETONE; CUMENE; DICHLOROBENZENE; ETHYLBENZENE; IRON CHLORIDE; MESITYLENE; MICROWAVE IRRADIATION;

ACYLATION;

BENZENE DERIVATIVE; FERROUS CHLORIDE; TOLUENE;

ACYLATION; ARTICLE; MICROWAVE RADIATION; MOLECULAR INTERACTION; REACTION ANALYSIS; REACTION TIME; TEMPERATURE;

EID: 0033627449     PISSN: 08885885     EISSN: None     Source Type: Journal    
DOI: 10.1021/ie9908884     Document Type: Article

References (81)

1. Part 2: Laporte, C.; Marquié, J.; Laporterie, A.; Desmurs, J. R.; Dubac, J. Réactions d'Acylation sous Irradiation Micro-onde. II. Acylation d'Ethers Aromatiques. C. R. Acad. Sci. Paris, Ser. IIc, t. 2, 1999, 455.
2. (a) Olah, G. A. Friedel - Crafts and Related Reactions; Wiley-Interscience: New York, 1964.
3. (b) Olah, G. A. Friedel - Crafts Chemistry; Wiley-Interscience: New York, 1973;
4. (c) Heaney, H. The Bimolecular Aromatic Friedel - Crafts Reaction. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, Chapter 3.2, pp 733-752.
5. (d) Taylor R. Electrophilic Aromatic Substitution; Wiley-Interscience: Chichester, 1990; pp 222-238.
6. (a) Pearson, D. E.; Buehler, C. A. Friedel - Crafts Acylations with Little or No Catalyst. Synthesis 1972, 533.
7. (b) Scheele, J. J. Electrophilic Aromatic Acylation. Ph.D. Thesis, Tech. Hogesch, Delft, The Netherlands, 1991; Chem. Abstr. 1992, 117, 130844y.
8. (c) Desbois, M.; Gallo, R.; Scuotto, J. F. (Rhône-Poulenc Spécialités Chimiques). Phenyl Ketones. French Patents 17,692 and 17,693, 1982; Chem. Abstr. 1984, 101, 130398a and 130399b.
9. (d) Effenberger, F.; Steegmüller, D. Electrophilic Aromatic Substitution. 33. Ferric Chloride Catalyzed Acylation of Aromatic Compounds with N-Phthaloyl α-Amino Acid Chlorides without Racemization. Chem. Ber. 1988, 121, 117.
10. (e) Effenberger, F.; Steegmüller, D.; Null, V.; Ziegler, T. Electrophilic Aromatic Substitution. 34. Intramolecular Friedel - Crafts Acylation of N-Phthaloyl-Substituted Arylalanyl and Homophenylalanyl Chlorides. Chem. Ber. 1988, 121, 125.
11. (a) Cornélis, A.; Gerstmans, A.; Laszlo, P.; Mathy, A.; Zieba, I. Friedel - Crafts Acylations with Modified Clays as Catalysts. Catal. Lett. 1990, 6, 103.
12. (b) Cornélis, A;, Laszlo, P.; Wang, S. On the Transition State for Clayzic-Catalyzed Friedel - Crafts Reaction upon Anisole. Tetrahedron Lett. 1993, 34, 3849.
13. (c) Clark, J. H.; Culle, S. R.; Barlow, S. J.; Bastock, T. W. Environmentally Friendly Chemistry Using Supported Reagent Catalysts: Structure -Property Relationships for Clayzic. J. Chem. Soc., Perkin Trans. 2 1994, 1117.
14. (a) Dubac, J.; Labrouillère, M.; Laporterie, A.; Desmurs, J. R. (Rhône-Poulenc Chimie). Preparation of Alkoxyaromatic Alkyl Ketones. European Patent Application EP 698,593, 1996 (French Application 94/10, 253); Chem. Abstr. 1996, 124, 316758y.
15. (b) Desmurs, J. R.; Labrouillère, M.; Dubac, J.; Laporterie, A.; Gaspard, H.; Metz, F. Bismuth(III) Salts in Friedel - Crafts Acylation. Industrial Chemistry Library; The Roots of Organic Development; Elsevier: Amsterdam, 1996; Vol. 8, pp 15-28.
16. Pivsa-Art, S.; Okuro, K.; Miura, M.; Murata, S.; Nomura, M. Acylation of 2-Methoxynaphthalene with Acyl Chlorides in the Presence of a Catalytic Amount of Lewis Acid. J. Chem. Soc., Perkin Trans 1 1994, 1703.
17. (a) Olah, G. A. Superelectrophiles. Angew. Chem., Int. Ed. Engl. 1993, 32, 767.
18. (b) Yato, M.; Ohwada, T.; Shudo, K. Requirements for the Houben-Hoesch and Gatterman Reactions. Involvement of Diprotonated Cyanides in the Reactions with Benzene. J. Am. Chem. Soc. 1991, 113, 691.
19. (c) Sato, Y.; Yato, M.; Ohwada, T.; Saito, S.; Shudo K. Involvment of Dicationic Species as the Reactive Intermediates in Gatterman, Houben-Hoesh and Friedel -Crafts Reactions of Nonactivated Benzenes. J. Am. Chem. Soc. 1995, 117, 3037.
20. (a) Effenberger, F.; Epple, G. Catalytic Friedel - Crafts Acylation of Aromatic Compounds. Angew. Chem., Int. Ed. Engl. 1972, 11, 300.
21. (b) Effenberger, F.; Sohn, E.; Epple, G. Electrophilic Aromatic Substitution. 25. Carboxylic Trifluoromethanesulfonic Anhydrides as Highly Effective Acylation Agents. Perfluoroalkanesulfonic Acid-Catalyzed Acylation of Arenes. Chem. Ber. 1983, 116, 1195.
22. (c) Effenberger, F.; Eberhard, J. K.; Maier, A. H. The First Unequivocal Evidence of the Reacting Electrophile in Aromatic Acylation Reactions. J. Am. Chem. Soc. 1996, 118, 12572.
23. (d) Izumi, J.; Mukaiyama, T. The Catalytic Friedel - Crafts Acylation Reaction of Aromatic Compounds with Carboxylic Anhydrides Using Combined Catalysts System of Titanium(IV) Chloride Tris(trifluoromethanesulfonate) and Trifluoromethanesulfonic Acid. Chem. Lett. 1996, 739.
24. (a) Hölderich, W.; Hesse, M.; Näumann, F. Zeolites: Catalysts for Organic Syntheses. Angew. Chem., Int. Ed. Engl. 1988, 27, 226.
25. (b) Akporiaye, D. E.; Daasvatn, K.; Solberg, J.; Stöcker, M. Modified Zeolites as Active Catalysts in Friedel - Crafts Acylation. Stud. Surf. Sci. Catal. 1993, 78 (Heterogeneous Catalysis and Fine Chemicals III), 521.
26. (c) Spagnol, M.; Gilbert, L.; Alby, D. Friedel - Crafts Acylation of Aromatics Using Zeolites. Industrial Chemistry Library; The Roots of Organic Development; Elsevier: Amsterdam, 1996; Vol. 8, pp 29-38.
27. 3 and a Silver Salt. Chem. Lett. 1991, 1059.
28. 4) in the Friedel - Crafts Acylation Reaction. Chem. Lett. 1992, 435.
29. (c) Suzuki, K.; Kitagawa, H.; Mukaiyama, T. The Catalytic Friedel - Crafts Acylation Reaction Starting from Aromatic Compounds and Free Carboxylic Acids (or Their Trimethylsilyl Esters) by Promotion of Silicon(IV) Cationic Species via Mixed Anhydrides. Bull. Chem. Soc. Jpn. 1993, 66, 3729.
30. Olah, G. A.; Farook, O.; Morteza, S.; Farnia, F.; Olah, J. Boron, Aluminium and Gallium Tris(trifluoromethanesulfonate) (Triflate): Effective New Friedel - Crafts Catalysts. J. Am. Chem. Soc. 1988, 110, 2560.
31. (a) Kawada, A.; Mitamura, S.; Kobayashi, S. Lanthanide Trifluoromethanesulfonates as Reusable Catalysts: Catalytic Friedel - Crafts Acylation. J. Chem. Soc., Chem. Commun. 1993, 1157.
32. (b) Kawada, A.; Mitamura, S.; Kobayashi, S. Scandium Trifluoromethanesulfonate. A Novel Catalyst for Friedel - Crafts Acylation. Synlett 1994, 545.
33. (a) Dubac, J.; Gaspard, H.; Labrouillère, M.; Laporterie, A.; Desmurs, J. R.; Le Roux, C. (Rhône-Poulenc Chimie). Preparation of Acylaromatics. PCT Internation Application WO 11,930, 1997 (French Application 95/11, 2501; Chem. Abstr. 1997, 126, 317246h.
34. (b) Desmurs, J. R.; Labrouillère, M.; Le Roux, C.; Laporterie, A.; Dubac J. Surprising Catalytic Activity of Bismuth(III) Triflate in the Friedel - Crafts Acylation Reaction. Tetrahedron Lett. 1997, 38, 8871.
35. (c) Répichet, S.; Le Roux, C.; Dubac, J.; Desmurs, J. R. Bismuth(III) Trifluoromethanesulfonate: A Chameleon Catalyst for the Friedel - Crafts Acylation. Eur. J. Org. Chem. 1998, 2743, 3.
36. (a) Mikami, K.; Kotera, O.; Motoyama, Y.; Sakaguchi, H.; Maruta, M. Metal Bis(trifluoromethylsulfonyl)amides as Highly Efficient Lewis Acid Catalysts for Acylation Reactions. Synlett 1996, 171.
37. (b) Central Glass Co., Ltd. Preparation of Acyl Compounds by Acylation with Acid Anhydrides in the Presence of Metal Compounds Having Bis(perfluoroalkanesulfonyl)amino Group. Japan Kokai Tokkyo Koho JP 09 169 690 [97 169 690]; Chem Abstr. 1997, 127, 95088n.
38. Nie, J.; Xu, J.; Zhou, G. Studies of the Lewis Acidity of Lanthanide Bis(trifluoromethyl)sulfonylamides and Lanthanide Bis(1,1,1,1,3,3,3-hexafluoro-2-propoxy)-sulfonylamides. J. Chem. Res. (S) 1999, 446.
39. (a) Hachiva, I.; Moriwaki, M.; Kobayashi, S. Catalytic Friedel - Crafts Acylation Reactions Using Hafnium Triflate as a Catalyst in Lithium Perchlorate-Nitromethane. Tetrahedron Lett. 1995, 38, 409.
40. (b) Hachiva, I.; Moriwaki, M.; Kobayashi, S. Hafnium(IV)Trifluoromethanesulfonate, An Efficient Catalyst for the Friedel - Crafts Acylation and Alkylation Reactions. Bull. Chem. Soc. Jpn. 1995, 68, 2053.
41. (c) Kobayashi, S.; Iwamoto, S. Catalytic Friedel - Crafts Acylation of Benzene, Chlorobenzene, and Fluorobenzene Using a Novel Catalyst System, Hafnium Triflate and Trifluoromethanesulfonic Acid. Tetrahedron Lett. 1998, 39, 4697.
42. Kusama, H.; Narasaka, K. Friedel - Crafts Acylation of Arenes Catalyzed by Bromopentacarbonylrhenium(I). Bull. Chem. Soc. Jpn. 1995, 68, 2379.
43. (a) Audhuy-Peaudecerf, M.; Berlan, J.; Dubac, J.; Laporterie, A.; Laurent, R.; Lefeuvre, S. Procédé pour réaliser la synthèse d'un ou de composés organiques ou organométalliques et applications notamment aux réactions d'acylation, réactions de redistribution et réactions péricycliques. French Patent 09,073, 1994.
44. (b) Laporte, C.; Baulès, P.; Laporterie, A.; Desmurs, J. R.; Dubac, J. Acylation d'aromatiques sous irradiation micro-onde en présence de graphite. C. R. Acad. Sci. Paris, Ser. IIc, t. 1, 1998, 141.
45. (a) Bram, G.; Loupy, A.; Majdoub, M.; Petit, M. Anthraquinone Microwave-Induced Synthesis in Dry Media in Domestic Ovens. Chem. Ind. 1991, 396.
46. (b) Acosta, A.; De la Cruz, P.; De Miguel, P.; Diez-Barra, E.; De la Hoz, A.; Langa, F.; Loupy, A.; Majdoub, M.; Martin, N.; Sanchez, C.; Seoane, C. Microwave Assisted Synthesis of Heterocyclic Fused Quinones in Dry Media. Tetrahedron Lett. 1995, 36, 2165.
47. (c) Filip, S. V.; Surducan, E.; Vlassa, M.; Silberg, I. A.; Jucan, G. Microwave-Assisted Acridone Preparation Using An Inorganic Acidic Solid Support. Heterocyclic Commun. 1996, 2, 431.
48. (d) Ranu, B. C.; Ghosh, K.; Jana, U. Simple and Improved Procedure for Regioselective Acylation of Aromatic Ethers with Carboxylic Acids on the Solid Surface of Alumina in the Presence of Trifluoroacetic Anhydride. J. Org. Chem. 1996, 61, 9546.
49. (e) Sridar, V.; Rao, V. S. S. Microwave-Induced Rate Enhancement of Fries Rearrangement. Ind. J. Chem. 1994, 33B, 184.
50. McClellan, A. L. Tables of Experimental Dipole Moments; Freeman: San Francisco, 1963; Vol. 1; Rahara Enterprises: El Cerrito, CA, 1974; Vol. 2.
51. Desmurs, J. R.; Dubac, J.; Laporterie, A.; Laporte, C.; Marquié, J. (Rhodia Chimie). Procédé d'acylation et de sulfonylation d'un composé aromatique. PCT International Application WO 40,339, 1998 (French Application 97/02917); Chem. Abstr. 1998, 129, 244928g.
52. Hansch, C.; Leo, A.; Taft, R. W. A Survey of Hammett Substituent Constants and Resonance and Field Parameters. Chem. Rev. 1991, 91, 165.
53. (a) Loupy, A.; Haudrechy, A. Effets de Milieu en Synthèse Organique; Masson: Paris, 1996; pp 277-305.
54. (b) Roussy, G.; Pearce, J. A. Foundations and Industrial Applications of Microwaves and Radio Frequency Fields; Wiley: Chichester, 1995; pp 445-466;
55. (c) Loupy, A.; Haudrechy, A. Les micro-ondes en synthèse organique: une méthodologie propre, performante et économique. In Méthodes et techniques de la chimie organique; Presses Universitaires de Grenoble: France, 1999; Chapter 6, pp 239-277.
56. Gore, P. H. Aromatic Ketone Synthesis. In Friedel - Crafts and Related Reactions; Wiley-Interscience: New York, 1964; Vol. 3, Chapter 31, pp 1-381 (p 39).
57. Agranat, I.; Shih, Y.-S.; Bentor, Y. Incursion of Reversibility in Friedel - Crafts Acylations. J. Am. Chem. Soc. 1974, 96, 1259.
58. Reference 2a, Vol. 1, Chapter 12, pp 937-997.
59. Ashforth, R.; Desmurs, J. R. Friedel - Crafts Acylation: Interaction Between Lewis Acids/Acyl Chlorides and Lewis Acids/ Aryl Ketones. Industrial Chemistry Library; The Roots of Organic Development; Elsevier: Amsterdam, 1996; Vol. 8, pp 3-14.
60. Recent compilative articles concerning the question of the nonthermal effect of MW in the rate of organic reactions: (a) Gedye, R. N.; Wei, J. B. Rate Enhancement of Organic Reactions by Microwaves at Atmospheric Pressure. Can. J. Chem. 1998, 76, 525.
61. (b) Gedye, R. N. The Question of Non-Thermal Effects in the Rate Enhancement of Organic Reactions by Microwaves. Ceram. Trans. 1997, 80, 165. Recent reviews concerning applications of MW technique in organic chemistry:
62. (c) Loupy, A.; Petit, A.; Hamelin, J.; Texier-Boullet, F.; Jacquault, P.; Mathé, D. New Solvent-Free Organic Synthesis Using Focused Microwaves. Synthesis 1998, 1213.
63. (d) Deshayes, S.; Liagre, M.; Loupy, A.; Luche, J.-L.; Petit, A. Microwave Activation in Phase Transfer Catalysis. Tetrahedron 1999, 55, 10851.
64. (e) Loupy, A. Solvent-Free Reactions. In Topics in Current Chemistry; Knochel, P., Ed.; Modern Solvents in Organic Synthesis; 1999; Vol. 206, pp 185-204. See also refs 22a and 22c.
65. (a) Gutierrez, E.; Loupy, A.; Bram, G.; Ruiz-Hitzky, E. Inorganic Solids in Dry Media. An Efficient Way for Developing Microwave Irradiation Activated Organic Reactions. Tetrahedron Lett. 1989, 30, 945.
66. (b) Bram, G.; Loupy, A.; Majdoub, M.; Gutierrez, E.; Ruiz-Hitzky, E. Alkylation of Potassium Acetate in Dry Media. Thermal Activation in Commercial Microwave Ovens. Tetrahedron 1990, 46, 5167.
67. (a) Loupy, A.; Pigeon, P.; Ramdani, M.; Jacquault, P. Solid - Liquid-Phase Transfer Catalysis Without Solvent Coupled with Microwave Irradiation: A Quick and Efficient Method for Saponification of Esters. Synth. Commun. 1994, 159.
68. (b) Loupy, A.; Pigeon, P.; Ramdani, M. Synthesis of Long Chain Aromatic Esters in a Solvent-Free Procedure Under Microwaves. Tetrahedron 1996, 52, 6705.
69. Carrillo-Munoz, J. R.; Bouvet, D.; Guibé-Jambel, E.; Loupy, A.; Petit, A. Microwave-Promoted Lipase-Catalyzed Reactions. Resolution of (±)-1-Phenylethanol. J. Org. Chem. 1996, 61, 7746.
70. Reference 3b, p 64.
71. McEvoy, F. J.; Albright, J. D. Alkylations and Acylations of α-Aryl-4-morpholineacetonitriles (Masked Acyl Anion Equivalents) and Their Use in 1,4-Additions. J. Org. Chem. 1979, 44, 4597.
72. Bunnett, J. F.; Hrutfiord, B. F. Cleavage of o-Halobenzophenones by Potassium Amide in Liquid Ammonia. J. Org. Chem. 1962, 27, 4152.
73. Brown, H. C.; Young, H. L. Isomer Distribution in the Aluminium Chloride-Catalyzed Benzoylation of Toluene in Nitrobenzene. J. Org. Chem. 1957, 22, 719.
74. Bachmann, W. E.; Carlson, E., Jr.; Moran, J. C. The Effect of Halogen Atoms and of Alkyl Groups on the Rates of Dissociation of Pentaarylethanes. J. Org. Chem. 1948, 13, 916.
75. McCarty, F. J.; Tilford, C. H.; Van Campen, M. G., Jr. Central Stimulants. α,α-Disubstituted 2-Piperidinemethanols and 1,1-Disubstituted Heptahydroöxazolo[3,4-a]pyridines J. Am. Chem. Soc. 1957, 79, 472.
76. Gravatt, G. L.; Baguley, B. C.; Wilson, W. R.; Denny, W. A. DNA-Directed Alkylating Agents. 4. 4-Anilinoquinoline-Based Minor Groove Directed Aniline Mustards. J. Med. Chem. 1991, 34, 1552.
77. Joshi, K. C.; Giri, S. Organic Pesticides. (XIII). Synthesis of Some Fluoroketones and Their Thiosemicarbazones. J. Indian Chem. Soc. 1963, 40, 42.
78. Keumi, T.; Saga, H.; Taniguchi, R.; Kitajima, H. Application of 2-Trifluoromethanesulfonyloxypyridine in Trifluoroacetic Acid to Acylation of Aromatics. Chem. Lett. 1977, 1099.
79. Wiegers, K. E.; Smith, S. G. Kinetics and Mechanism of Lithium Aluminium Hydride and Lithium Alkoxyaluminohydride Reduction of Ketones in Diethyl Ether. J. Am. Chem. Soc. 1977, 99, 1480.
80. Araki, M.; Mukaiyama, T. Reaction of Mixed Carboxylic Anhydrides with Grignard Reagents. Useful Method for the Preparation of Ketones. Chem. Lett. 1974, 663.
81. Fountain, K. R.; Heinze, P.; Sherwood, M.; Maddex, D.; Gerhardt, G. Acylation of Aromatic Substrate with Ketenes. An Example of Vinyl Oxocation Reactivity. Can. J. Chem. 1980, 58, 1198.