Convenient Processes for the Synthesis of Aromatic Ketones from Aryl Bromides and Carboxylic Anhydrides Using a Cobalt Catalysis

Journal of Organic Chemistry

Volumn 69, Issue 3, 2004, Pages 936-942

  Kazmierski, Igor ^a   Bastienne, Mylène ^a   Gosmini, Corinne ^a   Paris, Jean Marc ^b   Périchon, Jacques ^a  

^a CNRS Université Paris Est Créteil Val de Marne   (France)

^b avenue des Freres Perret   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE COMPOUNDS; CARBOXYLIC ACIDS; CATALYSIS; COBALT;

AROMATIC ORGANOZINC REAGENT;

KETONES;

ACID ANHYDRIDE; AROMATIC COMPOUND; BROMIDE; CARBOXYLIC ACID DERIVATIVE; COBALT; KETONE; METAL COMPLEX; ORGANOMETALLIC COMPOUND; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; REAGENT; ZINC DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CROSS COUPLING REACTION; ELECTRON; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0842264108     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0352169     Document Type: Article

References (69)

1. Olah, G. A. Friedel-Crafts and Related Reactions; Interscience Publishing: New York, 1963; Vol. 1.
2. (a) For a review of acylation of organometallic reagents with acid chlorides, see: Dieter, R. K. Tetrahedron 1999, 55, 4177-4236.
3. (b) Acylation of alkyl cadmium reagents with anhydrides: De Benneville, P. L. J. Org. Chem. 1941, 6, 462-464.
4. (c) Acylation of alkyllithium reagents: Degani, I.; Dughera, S.; Fochi, R.; Serra, E. J. Org. Chem. 1996, 61, 9572-9577.
5. (d) Acylation of phenylsulfonylindoles: Jiang, J.; Gribble, G. W. Synth. Commun. 2002, 32, 2035-2040.
6. (a) Sato, F.; Inoue, M.; Oguro, K.; Sato, M. Tetrahedron Lett. 1979, 4303-4306.
7. (b) Erbele, M. K.; Kahle, G. G. Tetrahedron Lett. 1980, 21, 2303-2304.
8. Tucker, C. E.; Majid, T. N.; Knochel, P. J. Am. Chem. Soc. 1992, 114, 3983-3985.
9. For a review of organocopper chemistry, see: Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135-631.
10. Reactions of arylmanganese reagents with acid chlorides and anhydrides: (a) Cahiez, G.; Bernard, D.; Normant, J. F. Synthesis 1977, 130-133.
11. (b) Friour, G.; Cahiez, G.; Normant, J. F. Synthesis 1984, 37-40.
12. (c) Friour, G.; Cahiez, G.; Normant, J. F. Synthesis 1985, 50-54.
13. (d) Cahiez, G.; Laboue, B. Tetrahedron Lett. 1989, 27, 3545-3546.
14. (e) Cahiez, G.; Laboue, B. Tetrahedron Lett. 1989, 30, 7369-7372.
15. Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524.
16. Reactions of organozinc reagents with acid chlorides, palladium catalysis: (a) Negishi, E.; Bagheri, V.; Chatterjee, S.; Luo, F. T.; Miller, J. A.; Miller, A. T. Tetrahedron Lett. 1983, 24, 5181-5184.
17. (b) Grey, R. A. J. Org. Chem. 1984, 49, 2288-2289.
18. Copper catalysis: (c) Knochel, P.; Yeh, M. C. P.; Berk, S. C.; Talbert, J. J. Org. Chem. 1988, 53, 2390-2392.
19. Reactions of arylboronic acids with acid chlorides: (a) Haddach, M.; McCarthy, J. R. Tetrahedron Lett. 1999, 40, 3109-3112.
20. (b) Bumagin, N. A.; Korolev, D. N. Tetrahedron Lett. 1999, 40, 3057-3060.
21. Reactions of arylboronic acids with acid anhydrides: (c) L. J. Goossen, Ghosh, K. Angew. Chem., Int. Ed. 2001, 40, 3458-3460.
22. (d) Kakino, R.; Yasumi, S.; Shimizu, I.; Yamamoto, A. Bull. Chem. Soc. Jpn. 2002, 75, 137-148.
23. Preparation of organocopper reagents by transmetalation: (a) Wipf, P. Synthesis 1993, 537-557.
24. (b) Dohle, W.; Lindsay, D. H.; Knochel, P. Org. Lett. 2001, 3, 2871-2873.
25. Preparation of organozinc reagents: (a) Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117-2188.
26. (b) Knochel, P.; Almena Prea, J. J.; Jones, P. Tetrahedron 1998, 54, 8275-8319.
27. (c) Boudier, A.; Bromm, L. O.; Lotz, M.; Knochel, P. Angew. Chem., Int. Ed. 2000, 39, 4414-4435.
28. (d) Jensen, A. E.; Dohle, W.; Sapountzis, I.; Lindsay, D. M.; Vu, V. A.; Knochel, P. Synthesis 2002, 565-569.
29. (e) Kneisel, F. F.; Knochel, P. Synlett 2002, 1799-1802.
30. (a) Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508-7510.
31. (b) Ishiyama, T.; Itoh, Y.; Kitano, T.; Miyaura, N. Tetrahedron Lett. 1997, 38, 3447-3450.
32. (c) Murata, M.; Watanabe, S.; Masuda, Y. J. Org. Chem. 1997, 62, 6458-6459.
33. (d) Baudoin, O.; Guénard, D.; Guéritte, F. J. Org. Chem. 2000, 65, 9268-9271.
34. (e) Ishiyama, T.; Ishida, K.; Miyaura, N. Tetrahedron 2001, 57, 9813-9816.
35. (a) Rieke, R. D.; Hanson, M. V. Tetrahedron 1997, 53, 1925-1956.
36. (b) Kim, S. H.; Hanson, M. V.; Rieke, R. D. Tetrahedron Lett. 1996, 37, 2197-2200.
37. (a) Fürstner, A.; Brunner, H. Tetrahedron Lett. 1996, 37, 7009-7012.
38. (b) Cahiez, G.; Martin, A.; Delacroix, T. Tetrahedron Lett. 1999, 40, 6407-6410.
39. (a) Boudier, A.; Bromm, L. O.; Lotz, M.; Knochel, P. Angew. Chem., Int. Ed. 2000, 39, 4414-4435.
40. (b) Knochel, P.; Dohle, W.; Gommermann, N.; Kneisel, F. F.; Kopp, F.; Korn, T.; Sapountzis, I.; Vu, V. A. Angew. Chem., Int. Ed. 2003, 42, 4302-4320.
41. (a) Fillon, H.; Gosmini, C.; Périchon, J. J. Am. Chem. Soc. 2003, 125, 3867-3870.
42. (b) Fillon, H.; Gosmini, C.; Périchon, J. Patent Application 01/08880, France, July 4, 2001.
43. Fillon, H.; Gosmini, C.; Périchon, J. Tetrahedron 2003, 59, 8199-8202.
44. Kazmierski, I.; Gosmini, C.; Périchon, J. Tetrahedron Lett. 2003, 44, 6417-6420.
45. (a) Devasagayaraj, A.; Knochel, P. Tetrahedron Lett. 1995, 36, 8411-8414.
46. (b) Reddy, C. K.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1700-1701.
47. Seka, S.; Buriez, 0.; Nedelec, J. Y.; Périchon, J. Chem. Eur. J. 2002, 8, 2534-2538.
48. Corain, B.; Favero, G. J. Chem. Soc., Dalton. Trans. 1975, 283-285.
49. Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165-195.
50. Citterio, A.; Serravalle, M.; Vismara, E. Tetrahedron Lett. 1982, 23, 1831-1834.
51. Usami, K.; Isobe, M. Tetrahedron 1996, 52, 12061-2090.
52. Mirarchi, D.; Ritchie, G. L. D. Aust. J. Chem. 1981, 34, 1443-1450.
53. Lijser, H. J. P.; Arnold, D. R. J. Chem. Soc., Perkin Trans. 2 1997, 7, 1369-1380.
54. Tanaka, K.; Katsuada, M.; Ohno, F.; Shiga, Y.; Oda, M.; Miyagi, M.; Takehara, J.; Okano, K. J. Org. Chem. 2000, 65, 432-437.
55. Brownlee, R. T. C.; Craik, D. J. Aust. J. Chem. 1980, 33, 2555-2559.
56. Vogel's Textbook of Practical Organic Chemistry, 5th ed.; Longman Scientific & Technical: Essex, UK, 1989.
57. Rieke, R. D.; Klein, W. R.; Wu, T. C. J. Org. Chem. 1993, 58, 2492-2500.
58. Hwang, J. P.; Prakash, G. K. S.; Olah, G. A. Tetrahedron 2000, 56, 7199-7204.
59. Wagner, P. J.; Siebert, E. J. J. Am. Chem. Soc. 1981, 103, 7329-7335.
60. McEvoy, F. J.; Albright, J. D. J. Org. Chem. 1979, 44, 4597-4603.
61. Wagner, P. J.; Truman, R. J.; Puchalski, A. E.; Wake, R. J. Am. Chem. Soc. 1986, 108, 7727-7738.
62. Kubota, Y.; Nakada, S.; Sugi, Y. Synth. Lett. 1998, 183-185.
63. Zhu, L.; Wehmeyer, R. M.; Rieke, R. D. J. Org. Chem. 1991, 56, 1445-1453.
64. Brügel, W. Handbook of NMR Spectral Parameters; Heyden, 1979; Vol. 1, p 47.
65. Adams, D. J.; Clark, J. H.; McFarland, H. J. Fluorine Chem. 1998, 92, 127-129.
66. Pouchert, C. J. The Aldrich Library of NMR Spectra, ed. 2; 1983; Vol. 2.
67. Sancassan, F.; Petrillo, G.; Abraham, R. J. J. Chem. Soc., Perkin Trans. 2 1995, 11, 1965-1972.
68. Yamada, H. et al. Bull. Chem. Soc. Jpn. 1970, 43, 1459-1472.
69. Exner, O.; Budesinsky, M. Magn. Res. Chem. 1989, 27, 27-36.