Heck Arylation of 1,2-Cyclohexanedione and 2-Ethoxy-2-cyclohexenone

Journal of Organic Chemistry

Volumn 63, Issue 12, 1998, Pages 4158-4162

  Garg, Neeraj ^a   Larhed, Mats ^a   Hallberg, Anders ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001571950     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980221b     Document Type: Article

References (85)

1. For reviews on the Heck reaction see: (a) Heck, R. F. Org React. 1982, 27, 345. (b) Heck, R. F. Comprehensive Organic Synthesis; Trost, B. M., Flemming, I., Eds.; Pergamon Press: Oxford 1991; Vol. 4, p 833. (c) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (d) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2. (e) Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Chemistry; John Wiley & Sons: Chichester, 1995; p 125. (f) Soderberg, B. C. Comprehensive Organometallic Chemistry II; Hegedus, L. S., Volume Ed., Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford 1995; Vol. 12, p 259. (g) Jeffery, T. Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press Inc: Greenwich 1996; Vol. 5, p 153. (h) Bräse, S.; de Meijere, A. Metal-catalyzed Cross-Coupling Reactions; Stang, P. J., Diederich, F., Eds.; Wiley-VCH: Weinheim, 1997; p 99.
2. For reviews on the Heck reaction see: (a) Heck, R. F. Org React. 1982, 27, 345. (b) Heck, R. F. Comprehensive Organic Synthesis; Trost, B. M., Flemming, I., Eds.; Pergamon Press: Oxford 1991; Vol. 4, p 833. (c) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (d) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2. (e) Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Chemistry; John Wiley & Sons: Chichester, 1995; p 125. (f) Soderberg, B. C. Comprehensive Organometallic Chemistry II; Hegedus, L. S., Volume Ed., Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford 1995; Vol. 12, p 259. (g) Jeffery, T. Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press Inc: Greenwich 1996; Vol. 5, p 153. (h) Bräse, S.; de Meijere, A. Metal-catalyzed Cross-Coupling Reactions; Stang, P. J., Diederich, F., Eds.; Wiley-VCH: Weinheim, 1997; p 99.
3. For reviews on the Heck reaction see: (a) Heck, R. F. Org React. 1982, 27, 345. (b) Heck, R. F. Comprehensive Organic Synthesis; Trost, B. M., Flemming, I., Eds.; Pergamon Press: Oxford 1991; Vol. 4, p 833. (c) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (d) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2. (e) Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Chemistry; John Wiley & Sons: Chichester, 1995; p 125. (f) Soderberg, B. C. Comprehensive Organometallic Chemistry II; Hegedus, L. S., Volume Ed., Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford 1995; Vol. 12, p 259. (g) Jeffery, T. Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press Inc: Greenwich 1996; Vol. 5, p 153. (h) Bräse, S.; de Meijere, A. Metal-catalyzed Cross-Coupling Reactions; Stang, P. J., Diederich, F., Eds.; Wiley-VCH: Weinheim, 1997; p 99.
4. For reviews on the Heck reaction see: (a) Heck, R. F. Org React. 1982, 27, 345. (b) Heck, R. F. Comprehensive Organic Synthesis; Trost, B. M., Flemming, I., Eds.; Pergamon Press: Oxford 1991; Vol. 4, p 833. (c) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (d) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2. (e) Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Chemistry; John Wiley & Sons: Chichester, 1995; p 125. (f) Soderberg, B. C. Comprehensive Organometallic Chemistry II; Hegedus, L. S., Volume Ed., Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford 1995; Vol. 12, p 259. (g) Jeffery, T. Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press Inc: Greenwich 1996; Vol. 5, p 153. (h) Bräse, S.; de Meijere, A. Metal-catalyzed Cross-Coupling Reactions; Stang, P. J., Diederich, F., Eds.; Wiley-VCH: Weinheim, 1997; p 99.
5. For reviews on the Heck reaction see: (a) Heck, R. F. Org React. 1982, 27, 345. (b) Heck, R. F. Comprehensive Organic Synthesis; Trost, B. M., Flemming, I., Eds.; Pergamon Press: Oxford 1991; Vol. 4, p 833. (c) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (d) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2. (e) Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Chemistry; John Wiley & Sons: Chichester, 1995; p 125. (f) Soderberg, B. C. Comprehensive Organometallic Chemistry II; Hegedus, L. S., Volume Ed., Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford 1995; Vol. 12, p 259. (g) Jeffery, T. Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press Inc: Greenwich 1996; Vol. 5, p 153. (h) Bräse, S.; de Meijere, A. Metal-catalyzed Cross-Coupling Reactions; Stang, P. J., Diederich, F., Eds.; Wiley-VCH: Weinheim, 1997; p 99.
6. For reviews on the Heck reaction see: (a) Heck, R. F. Org React. 1982, 27, 345. (b) Heck, R. F. Comprehensive Organic Synthesis; Trost, B. M., Flemming, I., Eds.; Pergamon Press: Oxford 1991; Vol. 4, p 833. (c) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (d) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2. (e) Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Chemistry; John Wiley & Sons: Chichester, 1995; p 125. (f) Soderberg, B. C. Comprehensive Organometallic Chemistry II; Hegedus, L. S., Volume Ed., Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford 1995; Vol. 12, p 259. (g) Jeffery, T. Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press Inc: Greenwich 1996; Vol. 5, p 153. (h) Bräse, S.; de Meijere, A. Metal-catalyzed Cross-Coupling Reactions; Stang, P. J., Diederich, F., Eds.; Wiley-VCH: Weinheim, 1997; p 99.
7. For reviews on the Heck reaction see: (a) Heck, R. F. Org React. 1982, 27, 345. (b) Heck, R. F. Comprehensive Organic Synthesis; Trost, B. M., Flemming, I., Eds.; Pergamon Press: Oxford 1991; Vol. 4, p 833. (c) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (d) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2. (e) Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Chemistry; John Wiley & Sons: Chichester, 1995; p 125. (f) Soderberg, B. C. Comprehensive Organometallic Chemistry II; Hegedus, L. S., Volume Ed., Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford 1995; Vol. 12, p 259. (g) Jeffery, T. Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press Inc: Greenwich 1996; Vol. 5, p 153. (h) Bräse, S.; de Meijere, A. Metal-catalyzed Cross-Coupling Reactions; Stang, P. J., Diederich, F., Eds.; Wiley-VCH: Weinheim, 1997; p 99.
8. For reviews on the Heck reaction see: (a) Heck, R. F. Org React. 1982, 27, 345. (b) Heck, R. F. Comprehensive Organic Synthesis; Trost, B. M., Flemming, I., Eds.; Pergamon Press: Oxford 1991; Vol. 4, p 833. (c) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (d) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2. (e) Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Chemistry; John Wiley & Sons: Chichester, 1995; p 125. (f) Soderberg, B. C. Comprehensive Organometallic Chemistry II; Hegedus, L. S., Volume Ed., Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford 1995; Vol. 12, p 259. (g) Jeffery, T. Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press Inc: Greenwich 1996; Vol. 5, p 153. (h) Bräse, S.; de Meijere, A. Metal-catalyzed Cross-Coupling Reactions; Stang, P. J., Diederich, F., Eds.; Wiley-VCH: Weinheim, 1997; p 99.
9. (a) Andersson, C.-M.; Larsson, J.; Hallberg, A. J. Org. Chem. 1990, 55, 5757.
10. (b) Larhed, M.; Andersson, C.-M.; Hallberg, A. Acta Chem. Scand. 1993, 47, 212.
11. (c) Badone, D.; Guzzi, U. Tetrahedron Lett. 1993, 34, 3603.
12. (d) Larhed, M.; Andersson, C.-M.; Hallberg, A. Tetrahedron 1994, 50, 285.
13. (e) Larhed, M.; Hallberg, A. J. Org. Chem. 1997, 62, 7858.
14. Cacchi, S.; Ciattini, P. G.; Morera, E.; Ortar, G. Tetrahedron Lett. 1987, 28, 3039.
15. Hultén, J.; Bonham, N. M.; Nillroth, U.; Hansson, T.; Zuccarello, G.; Bouzide, A.; Åqvist, J.; Classon, B.; Danielson, U. H.; Karlén, A.; Kvarnström, I.; Samuelsson, B.; Hallberg, A. J. Med. Chem. 1997, 40, 885.
16. For carboxylic acid group isosteres see: (a) Korolkovas, A. Essentials of Medicinal Chemistry; John Wiley & Sons: Chichester 1988; p 81. (b) Silverman, R. B. The Organic Chemistry of Drug Design and Drug Action; Academic Press: San Diego 1992; p 20.
17. For carboxylic acid group isosteres see: (a) Korolkovas, A. Essentials of Medicinal Chemistry; John Wiley & Sons: Chichester 1988; p 81. (b) Silverman, R. B. The Organic Chemistry of Drug Design and Drug Action; Academic Press: San Diego 1992; p 20.
18. Relatively few examples are documented for the preparation of 3-aryl-1, 2-cyclohexanediones. Oxidations: (a) Goldblum, A.; Mechoulam, R. J. Chem. Soc., Perkin Trans. 1 1977, 1889. (b) Kawada, K.; Gross, R. S.; Watt, D. S. Synth. Commun. 1989, 19, 777. (c) Horiuchi, C. A.; Kiyomiya, H.; Takahashi, M.; Suzuki, Y. Synthesis 1989, 785. Photolysis: (d) Feigenbaum, A.; Pete, J.-P.; Scholler, D. J. Org. Chem. 1984, 49, 2355. (e) Feigenbaum, A.; Pete, J.-P.; Scholler, D. J. Org. Chem. 1986, 51, 4424. Conjugate addition: (f) Tomboulian, P.; Bloomquist, C. A. A. J. Org. Chem. 1959, 24, 1239. (g) Charonnat, J. A.; Mitchell, A. L.; Keogh, B. P. Tetrahedron Lett. 1990, 31, 315.
19. Relatively few examples are documented for the preparation of 3-aryl-1, 2-cyclohexanediones. Oxidations: (a) Goldblum, A.; Mechoulam, R. J. Chem. Soc., Perkin Trans. 1 1977, 1889. (b) Kawada, K.; Gross, R. S.; Watt, D. S. Synth. Commun. 1989, 19, 777. (c) Horiuchi, C. A.; Kiyomiya, H.; Takahashi, M.; Suzuki, Y. Synthesis 1989, 785. Photolysis: (d) Feigenbaum, A.; Pete, J.-P.; Scholler, D. J. Org. Chem. 1984, 49, 2355. (e) Feigenbaum, A.; Pete, J.-P.; Scholler, D. J. Org. Chem. 1986, 51, 4424. Conjugate addition: (f) Tomboulian, P.; Bloomquist, C. A. A. J. Org. Chem. 1959, 24, 1239. (g) Charonnat, J. A.; Mitchell, A. L.; Keogh, B. P. Tetrahedron Lett. 1990, 31, 315.
20. Relatively few examples are documented for the preparation of 3-aryl-1, 2-cyclohexanediones. Oxidations: (a) Goldblum, A.; Mechoulam, R. J. Chem. Soc., Perkin Trans. 1 1977, 1889. (b) Kawada, K.; Gross, R. S.; Watt, D. S. Synth. Commun. 1989, 19, 777. (c) Horiuchi, C. A.; Kiyomiya, H.; Takahashi, M.; Suzuki, Y. Synthesis 1989, 785. Photolysis: (d) Feigenbaum, A.; Pete, J.-P.; Scholler, D. J. Org. Chem. 1984, 49, 2355. (e) Feigenbaum, A.; Pete, J.-P.; Scholler, D. J. Org. Chem. 1986, 51, 4424. Conjugate addition: (f) Tomboulian, P.; Bloomquist, C. A. A. J. Org. Chem. 1959, 24, 1239. (g) Charonnat, J. A.; Mitchell, A. L.; Keogh, B. P. Tetrahedron Lett. 1990, 31, 315.
21. Relatively few examples are documented for the preparation of 3-aryl-1, 2-cyclohexanediones. Oxidations: (a) Goldblum, A.; Mechoulam, R. J. Chem. Soc., Perkin Trans. 1 1977, 1889. (b) Kawada, K.; Gross, R. S.; Watt, D. S. Synth. Commun. 1989, 19, 777. (c) Horiuchi, C. A.; Kiyomiya, H.; Takahashi, M.; Suzuki, Y. Synthesis 1989, 785. Photolysis: (d) Feigenbaum, A.; Pete, J.-P.; Scholler, D. J. Org. Chem. 1984, 49, 2355. (e) Feigenbaum, A.; Pete, J.-P.; Scholler, D. J. Org. Chem. 1986, 51, 4424. Conjugate addition: (f) Tomboulian, P.; Bloomquist, C. A. A. J. Org. Chem. 1959, 24, 1239. (g) Charonnat, J. A.; Mitchell, A. L.; Keogh, B. P. Tetrahedron Lett. 1990, 31, 315.
22. Relatively few examples are documented for the preparation of 3-aryl-1, 2-cyclohexanediones. Oxidations: (a) Goldblum, A.; Mechoulam, R. J. Chem. Soc., Perkin Trans. 1 1977, 1889. (b) Kawada, K.; Gross, R. S.; Watt, D. S. Synth. Commun. 1989, 19, 777. (c) Horiuchi, C. A.; Kiyomiya, H.; Takahashi, M.; Suzuki, Y. Synthesis 1989, 785. Photolysis: (d) Feigenbaum, A.; Pete, J.-P.; Scholler, D. J. Org. Chem. 1984, 49, 2355. (e) Feigenbaum, A.; Pete, J.-P.; Scholler, D. J. Org. Chem. 1986, 51, 4424. Conjugate addition: (f) Tomboulian, P.; Bloomquist, C. A. A. J. Org. Chem. 1959, 24, 1239. (g) Charonnat, J. A.; Mitchell, A. L.; Keogh, B. P. Tetrahedron Lett. 1990, 31, 315.
23. Relatively few examples are documented for the preparation of 3-aryl-1, 2-cyclohexanediones. Oxidations: (a) Goldblum, A.; Mechoulam, R. J. Chem. Soc., Perkin Trans. 1 1977, 1889. (b) Kawada, K.; Gross, R. S.; Watt, D. S. Synth. Commun. 1989, 19, 777. (c) Horiuchi, C. A.; Kiyomiya, H.; Takahashi, M.; Suzuki, Y. Synthesis 1989, 785. Photolysis: (d) Feigenbaum, A.; Pete, J.-P.; Scholler, D. J. Org. Chem. 1984, 49, 2355. (e) Feigenbaum, A.; Pete, J.-P.; Scholler, D. J. Org. Chem. 1986, 51, 4424. Conjugate addition: (f) Tomboulian, P.; Bloomquist, C. A. A. J. Org. Chem. 1959, 24, 1239. (g) Charonnat, J. A.; Mitchell, A. L.; Keogh, B. P. Tetrahedron Lett. 1990, 31, 315.
24. Relatively few examples are documented for the preparation of 3-aryl-1, 2-cyclohexanediones. Oxidations: (a) Goldblum, A.; Mechoulam, R. J. Chem. Soc., Perkin Trans. 1 1977, 1889. (b) Kawada, K.; Gross, R. S.; Watt, D. S. Synth. Commun. 1989, 19, 777. (c) Horiuchi, C. A.; Kiyomiya, H.; Takahashi, M.; Suzuki, Y. Synthesis 1989, 785. Photolysis: (d) Feigenbaum, A.; Pete, J.-P.; Scholler, D. J. Org. Chem. 1984, 49, 2355. (e) Feigenbaum, A.; Pete, J.-P.; Scholler, D. J. Org. Chem. 1986, 51, 4424. Conjugate addition: (f) Tomboulian, P.; Bloomquist, C. A. A. J. Org. Chem. 1959, 24, 1239. (g) Charonnat, J. A.; Mitchell, A. L.; Keogh, B. P. Tetrahedron Lett. 1990, 31, 315.
25. 1,2-Diketones have found widespread use in the syntheses of different heterocyclic compounds. For some examples, see the following. (a) Bredereck, H.; Gompper, R.; von Schuh, H. G.; Theilig, G. Angew. Chem. 1959, 71, 753. (b) Porter, A. E. A. Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Boulton, A. J., McKillop, A., Eds.; Pergamon Press: Oxford 1984; Vol. 3, p 157. (c) Christl, M.; Kraft, A. Angew. Chem., Int. Ed. Engl. 1988, 27, 1369. (d) Gupta, A. K.; Fu, X.; Snyder, J. P.; Cook, J. M. Tetrahedron 1991, 47, 3665. (e) Kiselyov, A. S. Tetrahedron Lett. 1995, 36, 493.
26. 1,2-Diketones have found widespread use in the syntheses of different heterocyclic compounds. For some examples, see the following. (a) Bredereck, H.; Gompper, R.; von Schuh, H. G.; Theilig, G. Angew. Chem. 1959, 71, 753. (b) Porter, A. E. A. Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Boulton, A. J., McKillop, A., Eds.; Pergamon Press: Oxford 1984; Vol. 3, p 157. (c) Christl, M.; Kraft, A. Angew. Chem., Int. Ed. Engl. 1988, 27, 1369. (d) Gupta, A. K.; Fu, X.; Snyder, J. P.; Cook, J. M. Tetrahedron 1991, 47, 3665. (e) Kiselyov, A. S. Tetrahedron Lett. 1995, 36, 493.
27. 1,2-Diketones have found widespread use in the syntheses of different heterocyclic compounds. For some examples, see the following. (a) Bredereck, H.; Gompper, R.; von Schuh, H. G.; Theilig, G. Angew. Chem. 1959, 71, 753. (b) Porter, A. E. A. Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Boulton, A. J., McKillop, A., Eds.; Pergamon Press: Oxford 1984; Vol. 3, p 157. (c) Christl, M.; Kraft, A. Angew. Chem., Int. Ed. Engl. 1988, 27, 1369. (d) Gupta, A. K.; Fu, X.; Snyder, J. P.; Cook, J. M. Tetrahedron 1991, 47, 3665. (e) Kiselyov, A. S. Tetrahedron Lett. 1995, 36, 493.
28. 1,2-Diketones have found widespread use in the syntheses of different heterocyclic compounds. For some examples, see the following. (a) Bredereck, H.; Gompper, R.; von Schuh, H. G.; Theilig, G. Angew. Chem. 1959, 71, 753. (b) Porter, A. E. A. Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Boulton, A. J., McKillop, A., Eds.; Pergamon Press: Oxford 1984; Vol. 3, p 157. (c) Christl, M.; Kraft, A. Angew. Chem., Int. Ed. Engl. 1988, 27, 1369. (d) Gupta, A. K.; Fu, X.; Snyder, J. P.; Cook, J. M. Tetrahedron 1991, 47, 3665. (e) Kiselyov, A. S. Tetrahedron Lett. 1995, 36, 493.
29. 1,2-Diketones have found widespread use in the syntheses of different heterocyclic compounds. For some examples, see the following. (a) Bredereck, H.; Gompper, R.; von Schuh, H. G.; Theilig, G. Angew. Chem. 1959, 71, 753. (b) Porter, A. E. A. Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Boulton, A. J., McKillop, A., Eds.; Pergamon Press: Oxford 1984; Vol. 3, p 157. (c) Christl, M.; Kraft, A. Angew. Chem., Int. Ed. Engl. 1988, 27, 1369. (d) Gupta, A. K.; Fu, X.; Snyder, J. P.; Cook, J. M. Tetrahedron 1991, 47, 3665. (e) Kiselyov, A. S. Tetrahedron Lett. 1995, 36, 493.
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32. For examples of Heck reactions proceeding in water or in water/organic solvent mixtures, see: (a) Bumagin, N. A.; More, P. G.; Beletskaya I. P. J. Organomet. Chem. 1989, 371, 397. (b) Zhang, H.-C.; Daves, G. D., Jr. Organometallics 1993, 12, 1499. (c) Jeffery, T. Tetrahedron Lett. 1994, 35, 3051. (d) Kiji, J.; Okano, T.; Hasegawa, T. J. Mol. Catal. A: Chem. 1995, 97, 73. (e) Crisp, G. T.; Gebauer, M. G. Tetrahedron 1996, 52, 12465. See also ref 20.
33. For examples of Heck reactions proceeding in water or in water/organic solvent mixtures, see: (a) Bumagin, N. A.; More, P. G.; Beletskaya I. P. J. Organomet. Chem. 1989, 371, 397. (b) Zhang, H.-C.; Daves, G. D., Jr. Organometallics 1993, 12, 1499. (c) Jeffery, T. Tetrahedron Lett. 1994, 35, 3051. (d) Kiji, J.; Okano, T.; Hasegawa, T. J. Mol. Catal. A: Chem. 1995, 97, 73. (e) Crisp, G. T.; Gebauer, M. G. Tetrahedron 1996, 52, 12465. See also ref 20.
34. For examples of Heck reactions proceeding in water or in water/organic solvent mixtures, see: (a) Bumagin, N. A.; More, P. G.; Beletskaya I. P. J. Organomet. Chem. 1989, 371, 397. (b) Zhang, H.-C.; Daves, G. D., Jr. Organometallics 1993, 12, 1499. (c) Jeffery, T. Tetrahedron Lett. 1994, 35, 3051. (d) Kiji, J.; Okano, T.; Hasegawa, T. J. Mol. Catal. A: Chem. 1995, 97, 73. (e) Crisp, G. T.; Gebauer, M. G. Tetrahedron 1996, 52, 12465. See also ref 20.
35. For examples of Heck reactions proceeding in water or in water/organic solvent mixtures, see: (a) Bumagin, N. A.; More, P. G.; Beletskaya I. P. J. Organomet. Chem. 1989, 371, 397. (b) Zhang, H.-C.; Daves, G. D., Jr. Organometallics 1993, 12, 1499. (c) Jeffery, T. Tetrahedron Lett. 1994, 35, 3051. (d) Kiji, J.; Okano, T.; Hasegawa, T. J. Mol. Catal. A: Chem. 1995, 97, 73. (e) Crisp, G. T.; Gebauer, M. G. Tetrahedron 1996, 52, 12465. See also ref 20.
36. For examples of Heck reactions proceeding in water or in water/organic solvent mixtures, see: (a) Bumagin, N. A.; More, P. G.; Beletskaya I. P. J. Organomet. Chem. 1989, 371, 397. (b) Zhang, H.-C.; Daves, G. D., Jr. Organometallics 1993, 12, 1499. (c) Jeffery, T. Tetrahedron Lett. 1994, 35, 3051. (d) Kiji, J.; Okano, T.; Hasegawa, T. J. Mol. Catal. A: Chem. 1995, 97, 73. (e) Crisp, G. T.; Gebauer, M. G. Tetrahedron 1996, 52, 12465. See also ref 20.
37. Attempts to use iodobenzene or 1-iodonaphthalene in the coupling reactions with 1,2-cyclohexanedione (1) and 2-ethoxy-2-cyclohexenone (4) were unsuccessful. In all reactions, with or without phosphine ligands (triphenylphosphine or tri-o-tolylphosphine), the formation of biaryls strongly dominated. We believe that the slow arylation of 1 and 4 may be attributed to difficulties in the migratory insertion and a fast concomitant biaryl generation with aryl iodides as arylating agents.
38. It has been suggested that the reactivity and stoichiometry of the oxidative addition products of aryl iodides and bromides are substantially different. Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1996, 61, 1133.
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46. (d) Langa, F.; de la Cruz, P.; de la Hoz, A.; Díaz-Ortiz, A.; Díez-Barra, E. Contemp. Org. Synth. 1997, 373.
47. For microwave-assisted Pd-catalyzed coupling reactions see: (e) Larhed, M.; Lindeberg, G.; Hallberg, A. Tetrahedron Lett. 1996, 37, 8219. (f) Larhed, M.; Hallberg, A. J. Org. Chem. 1996, 61, 9582. (g) Larhed, M.; Hoshino, M.; Hadida, S.; Curran, D. P.; Hallberg, A. J. Org. Chem. 1997, 62, 5583. (h) Díaz-Ortiz, A.; Prieto, P.; Vázquez. Synlett 1997, 269. (i) Li, J.; Mau, A. W.-H.; Strauss, C. R. J. Chem. Soc., Chem. Commun. 1997, 1275. (j) Wali, A.; Muthukumaru Pillai, S.; Satish, S. React. Kinet. Catal. Lett. 1997, 60, 189.
48. For microwave-assisted Pd-catalyzed coupling reactions see: (e) Larhed, M.; Lindeberg, G.; Hallberg, A. Tetrahedron Lett. 1996, 37, 8219. (f) Larhed, M.; Hallberg, A. J. Org. Chem. 1996, 61, 9582. (g) Larhed, M.; Hoshino, M.; Hadida, S.; Curran, D. P.; Hallberg, A. J. Org. Chem. 1997, 62, 5583. (h) Díaz-Ortiz, A.; Prieto, P.; Vázquez. Synlett 1997, 269. (i) Li, J.; Mau, A. W.-H.; Strauss, C. R. J. Chem. Soc., Chem. Commun. 1997, 1275. (j) Wali, A.; Muthukumaru Pillai, S.; Satish, S. React. Kinet. Catal. Lett. 1997, 60, 189.
49. For microwave-assisted Pd-catalyzed coupling reactions see: (e) Larhed, M.; Lindeberg, G.; Hallberg, A. Tetrahedron Lett. 1996, 37, 8219. (f) Larhed, M.; Hallberg, A. J. Org. Chem. 1996, 61, 9582. (g) Larhed, M.; Hoshino, M.; Hadida, S.; Curran, D. P.; Hallberg, A. J. Org. Chem. 1997, 62, 5583. (h) Díaz-Ortiz, A.; Prieto, P.; Vázquez. Synlett 1997, 269. (i) Li, J.; Mau, A. W.-H.; Strauss, C. R. J. Chem. Soc., Chem. Commun. 1997, 1275. (j) Wali, A.; Muthukumaru Pillai, S.; Satish, S. React. Kinet. Catal. Lett. 1997, 60, 189.
50. For microwave-assisted Pd-catalyzed coupling reactions see: (e) Larhed, M.; Lindeberg, G.; Hallberg, A. Tetrahedron Lett. 1996, 37, 8219. (f) Larhed, M.; Hallberg, A. J. Org. Chem. 1996, 61, 9582. (g) Larhed, M.; Hoshino, M.; Hadida, S.; Curran, D. P.; Hallberg, A. J. Org. Chem. 1997, 62, 5583. (h) Díaz-Ortiz, A.; Prieto, P.; Vázquez. Synlett 1997, 269. (i) Li, J.; Mau, A. W.-H.; Strauss, C. R. J. Chem. Soc., Chem. Commun. 1997, 1275. (j) Wali, A.; Muthukumaru Pillai, S.; Satish, S. React. Kinet. Catal. Lett. 1997, 60, 189.
51. For microwave-assisted Pd-catalyzed coupling reactions see: (e) Larhed, M.; Lindeberg, G.; Hallberg, A. Tetrahedron Lett. 1996, 37, 8219. (f) Larhed, M.; Hallberg, A. J. Org. Chem. 1996, 61, 9582. (g) Larhed, M.; Hoshino, M.; Hadida, S.; Curran, D. P.; Hallberg, A. J. Org. Chem. 1997, 62, 5583. (h) Díaz-Ortiz, A.; Prieto, P.; Vázquez. Synlett 1997, 269. (i) Li, J.; Mau, A. W.-H.; Strauss, C. R. J. Chem. Soc., Chem. Commun. 1997, 1275. (j) Wali, A.; Muthukumaru Pillai, S.; Satish, S. React. Kinet. Catal. Lett. 1997, 60, 189.
52. For microwave-assisted Pd-catalyzed coupling reactions see: (e) Larhed, M.; Lindeberg, G.; Hallberg, A. Tetrahedron Lett. 1996, 37, 8219. (f) Larhed, M.; Hallberg, A. J. Org. Chem. 1996, 61, 9582. (g) Larhed, M.; Hoshino, M.; Hadida, S.; Curran, D. P.; Hallberg, A. J. Org. Chem. 1997, 62, 5583. (h) Díaz-Ortiz, A.; Prieto, P.; Vázquez. Synlett 1997, 269. (i) Li, J.; Mau, A. W.-H.; Strauss, C. R. J. Chem. Soc., Chem. Commun. 1997, 1275. (j) Wali, A.; Muthukumaru Pillai, S.; Satish, S. React. Kinet. Catal. Lett. 1997, 60, 189.
53. The substantially shorter reaction times obtained under microwave heating is probably arising from rapid heating to high temperatures under pressurized conditions, rather than a result of a specific microwave effect. (a) Hájek, M. Collect. Czech. Chem. Commun. 1997, 62, 347. (b) Larhed, M., Ph.D. Thesis, Uppsala University, Oct. 1997. See also ref 14.
54. The substantially shorter reaction times obtained under microwave heating is probably arising from rapid heating to high temperatures under pressurized conditions, rather than a result of a specific microwave effect. (a) Hájek, M. Collect. Czech. Chem. Commun. 1997, 62, 347. (b) Larhed, M., Ph.D. Thesis, Uppsala University, Oct. 1997. See also ref 14.
55. Nonprotected enamines were recently reported to undergo intramolecular Heck reactions. Chen, C.-Y.; Lieberman, D. R.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. J. Org. Chem. 1997, 62, 2676.
56. A β-elimination over carbon and oxygen from a α-hydroxy σ-complex, to give a carbonyl group and a palladium hydride, has been proposed in the catalytic cycle of the Wacker process. Bäckvall, J. E., Akermark, B.; Ljunggren, S. O. J. Am. Chem. Soc. 1979, 101, 2411.
57. Genet, J. P.; Blart, E.; Savignac, M. Synlett 1992, 715.
58. The electrostatic repulsion between the coplanar carbonyl dipoles has been suggested to be more important for the enolization of 1 than the stabilization of the enol form by hydrogen bonding. Hammond, G. S. Steric effects in Organic Chemistry; Newman, M. S., Ed.; John Wiley and Sons: New York 1956; p 450.
59. For examples of isolated five-membered Pd(II) 1,2-diketonate complexes see: (a) Morita, H.; Sakurai, H.; Shimomura, S.; Kawaguchi, S. Transition Met. Chem. 1977, 2, 210. (b) Morita, H.; Shimomura, S.; Kawaguchi, S. Bull. Chem. Soc., Jpn. 1979, 52, 1838. (c) Greaves, S. J.; Griffith, W. P. Polyhedron 1988, 7, 1973. (d) Griffith, W. P.; Mostafa, S. I. Polyhedron 1992, 11, 2997.
60. For examples of isolated five-membered Pd(II) 1,2-diketonate complexes see: (a) Morita, H.; Sakurai, H.; Shimomura, S.; Kawaguchi, S. Transition Met. Chem. 1977, 2, 210. (b) Morita, H.; Shimomura, S.; Kawaguchi, S. Bull. Chem. Soc., Jpn. 1979, 52, 1838. (c) Greaves, S. J.; Griffith, W. P. Polyhedron 1988, 7, 1973. (d) Griffith, W. P.; Mostafa, S. I. Polyhedron 1992, 11, 2997.
61. For examples of isolated five-membered Pd(II) 1,2-diketonate complexes see: (a) Morita, H.; Sakurai, H.; Shimomura, S.; Kawaguchi, S. Transition Met. Chem. 1977, 2, 210. (b) Morita, H.; Shimomura, S.; Kawaguchi, S. Bull. Chem. Soc., Jpn. 1979, 52, 1838. (c) Greaves, S. J.; Griffith, W. P. Polyhedron 1988, 7, 1973. (d) Griffith, W. P.; Mostafa, S. I. Polyhedron 1992, 11, 2997.
62. For examples of isolated five-membered Pd(II) 1,2-diketonate complexes see: (a) Morita, H.; Sakurai, H.; Shimomura, S.; Kawaguchi, S. Transition Met. Chem. 1977, 2, 210. (b) Morita, H.; Shimomura, S.; Kawaguchi, S. Bull. Chem. Soc., Jpn. 1979, 52, 1838. (c) Greaves, S. J.; Griffith, W. P. Polyhedron 1988, 7, 1973. (d) Griffith, W. P.; Mostafa, S. I. Polyhedron 1992, 11, 2997.
63. a = 5.3). Beil. 7, E III, 3209.
64. 2 did not improve the yields.
65. We were aware of only one report on palladium-catalyzed intermolecular α-arylation of simple ketones while performing the synthetic work. (a) Hou, D.; Mas, J. L. U.S. Patent, 4992591, 1991. Chem. Abstr. 1991, 115, 28927z. After the completion of our laboratory work, four reports conducted under similar palladium-catalyzed conditions appeared in the literature. (b) Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 6, 1740. (c) Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108. (d) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382. (e) Åhman, J.; Wolfe, J. P.; Troutman, M. V.; Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 1918. In the general methods for direct α-arylation (a, c, d, and e) the use of a strong base is obligatory.
66. We were aware of only one report on palladium-catalyzed intermolecular α-arylation of simple ketones while performing the synthetic work. (a) Hou, D.; Mas, J. L. U.S. Patent, 4992591, 1991. Chem. Abstr. 1991, 115, 28927z. After the completion of our laboratory work, four reports conducted under similar palladium-catalyzed conditions appeared in the literature. (b) Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 6, 1740. (c) Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108. (d) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382. (e) Åhman, J.; Wolfe, J. P.; Troutman, M. V.; Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 1918. In the general methods for direct α-arylation (a, c, d, and e) the use of a strong base is obligatory.
67. We were aware of only one report on palladium-catalyzed intermolecular α-arylation of simple ketones while performing the synthetic work. (a) Hou, D.; Mas, J. L. U.S. Patent, 4992591, 1991. Chem. Abstr. 1991, 115, 28927z. After the completion of our laboratory work, four reports conducted under similar palladium-catalyzed conditions appeared in the literature. (b) Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 6, 1740. (c) Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108. (d) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382. (e) Åhman, J.; Wolfe, J. P.; Troutman, M. V.; Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 1918. In the general methods for direct α-arylation (a, c, d, and e) the use of a strong base is obligatory.
68. We were aware of only one report on palladium-catalyzed intermolecular α-arylation of simple ketones while performing the synthetic work. (a) Hou, D.; Mas, J. L. U.S. Patent, 4992591, 1991. Chem. Abstr. 1991, 115, 28927z. After the completion of our laboratory work, four reports conducted under similar palladium-catalyzed conditions appeared in the literature. (b) Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 6, 1740. (c) Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108. (d) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382. (e) Åhman, J.; Wolfe, J. P.; Troutman, M. V.; Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 1918. In the general methods for direct α-arylation (a, c, d, and e) the use of a strong base is obligatory.
69. We were aware of only one report on palladium-catalyzed intermolecular α-arylation of simple ketones while performing the synthetic work. (a) Hou, D.; Mas, J. L. U.S. Patent, 4992591, 1991. Chem. Abstr. 1991, 115, 28927z. After the completion of our laboratory work, four reports conducted under similar palladium-catalyzed conditions appeared in the literature. (b) Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 6, 1740. (c) Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108. (d) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382. (e) Åhman, J.; Wolfe, J. P.; Troutman, M. V.; Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 1918. In the general methods for direct α-arylation (a, c, d, and e) the use of a strong base is obligatory.
70. We were aware of only one report on palladium-catalyzed intermolecular α-arylation of simple ketones while performing the synthetic work. (a) Hou, D.; Mas, J. L. U.S. Patent, 4992591, 1991. Chem. Abstr. 1991, 115, 28927z. After the completion of our laboratory work, four reports conducted under similar palladium-catalyzed conditions appeared in the literature. (b) Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 6, 1740. (c) Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108. (d) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382. (e) Åhman, J.; Wolfe, J. P.; Troutman, M. V.; Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 1918. In the general methods for direct α-arylation (a, c, d, and e) the use of a strong base is obligatory.
71. See ref 1e, p 244.
72. (a) Uno, M.; Seto, K.; Takahashi, S. J. Chem. Soc., Chem. Commun. 1984, 932.
73. (b) Uno, M.; Seto, K.; Masuda, M.; Ueda, W.; Takahashi, S. Tetrahedron Lett. 1985, 26, 1553.
74. (c) Sakamoto, T.; Katoh, E., Kondo, Y.; Yamanaka, H. Chem. Pharm. Bull. 1988, 36, 1664.
75. (d) Sakamoto, T.; Kondo, Y.; Suginome, T.; Ohba, S.; Yamanaka, H. Synthesis 1992, 552.
76. Intermolecular arylations of soft carbon nucleophiles lacking cyano groups have been reported with aryl lead(IV) compounds, (a) Donnelly, D. M. X.; Finet, J.-P.; Rattigan, B. A. J. Chem. Soc., Perkin Trans. 1 1993, 1729, or with a copper(I) catalyst. (b) Okuro, K.; Furuune, M., Miura, M.; Nomura, M. J. Org. Chem., 1993, 58, 7606.
77. Intermolecular arylations of soft carbon nucleophiles lacking cyano groups have been reported with aryl lead(IV) compounds, (a) Donnelly, D. M. X.; Finet, J.-P.; Rattigan, B. A. J. Chem. Soc., Perkin Trans. 1 1993, 1729, or with a copper(I) catalyst. (b) Okuro, K.; Furuune, M., Miura, M.; Nomura, M. J. Org. Chem., 1993, 58, 7606.
78. For examples of Pd-catalyzed intramolecular arylations of enolate anions (from β-diketones or monoketones) see: (a) Ciufolini, M. A.; Qi, H.-B.; Browne, M. E. J. Org. Chem. 1988, 53, 4151. (b) Piers, E.; Marais, P. C. J. Org. Chem. 1990, 55, 3454. (c) Piers, E.; Renaud, J. J. Org. Chem. 1993, 58, 11. (d) Muratake, H.; Hayakawa, A.; Natsume, M. Tetrahedron Lett. 1997, 38, 7577. (e) Muratake, H.; Natsume, M. Tetrahedron Lett. 1997, 38, 7581.
79. For examples of Pd-catalyzed intramolecular arylations of enolate anions (from β-diketones or monoketones) see: (a) Ciufolini, M. A.; Qi, H.-B.; Browne, M. E. J. Org. Chem. 1988, 53, 4151. (b) Piers, E.; Marais, P. C. J. Org. Chem. 1990, 55, 3454. (c) Piers, E.; Renaud, J. J. Org. Chem. 1993, 58, 11. (d) Muratake, H.; Hayakawa, A.; Natsume, M. Tetrahedron Lett. 1997, 38, 7577. (e) Muratake, H.; Natsume, M. Tetrahedron Lett. 1997, 38, 7581.
80. For examples of Pd-catalyzed intramolecular arylations of enolate anions (from β-diketones or monoketones) see: (a) Ciufolini, M. A.; Qi, H.-B.; Browne, M. E. J. Org. Chem. 1988, 53, 4151. (b) Piers, E.; Marais, P. C. J. Org. Chem. 1990, 55, 3454. (c) Piers, E.; Renaud, J. J. Org. Chem. 1993, 58, 11. (d) Muratake, H.; Hayakawa, A.; Natsume, M. Tetrahedron Lett. 1997, 38, 7577. (e) Muratake, H.; Natsume, M. Tetrahedron Lett. 1997, 38, 7581.
81. For examples of Pd-catalyzed intramolecular arylations of enolate anions (from β-diketones or monoketones) see: (a) Ciufolini, M. A.; Qi, H.-B.; Browne, M. E. J. Org. Chem. 1988, 53, 4151. (b) Piers, E.; Marais, P. C. J. Org. Chem. 1990, 55, 3454. (c) Piers, E.; Renaud, J. J. Org. Chem. 1993, 58, 11. (d) Muratake, H.; Hayakawa, A.; Natsume, M. Tetrahedron Lett. 1997, 38, 7577. (e) Muratake, H.; Natsume, M. Tetrahedron Lett. 1997, 38, 7581.
82. For examples of Pd-catalyzed intramolecular arylations of enolate anions (from β-diketones or monoketones) see: (a) Ciufolini, M. A.; Qi, H.-B.; Browne, M. E. J. Org. Chem. 1988, 53, 4151. (b) Piers, E.; Marais, P. C. J. Org. Chem. 1990, 55, 3454. (c) Piers, E.; Renaud, J. J. Org. Chem. 1993, 58, 11. (d) Muratake, H.; Hayakawa, A.; Natsume, M. Tetrahedron Lett. 1997, 38, 7577. (e) Muratake, H.; Natsume, M. Tetrahedron Lett. 1997, 38, 7581.
83. Stone-Elander, S. A.; Blander, N.; Thorell, J.-O.; Solås, G.; Svennebrink, J. J. Label. Cmpds. Radiopharm. 1994, 10, 949.
84. a and log P has been described in detail. Avdeef, A. Lipophilicity in Drug Action and Toxicology; Pliska, V., Testa, B., van de Waterbeemd, H., Eds.; VCH: Weinheim, 1996; p 109.
85. Gannon, W. F.; House, H. O. Org. Synth. 1960, 40, 41.