Carbon - Carbon bond formation via palladium-catalyzed reductive coupling in air

Organic Letters

Volumn 1, Issue 7, 1999, Pages 1133-1135

  Venkatraman, Sripathy ^a   Li, Chao Jun ^a  

^a Tulane University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000198614     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9909740     Document Type: Article

References (37)

1. For representative reviews, see: Trost, B. M. Tetrahedron 1977, 33, 2615. Tsuji, J. Top. Curr. Chem. 1980, 91, 29. Kumada, M. Pure Appl. Chem. 1980, 52, 669. Negishi, E. I. Acc. Chem. Res. 1982, 15, 340. Tsuji, J. Organic Synthesis with Palladium Compounds; Springer-Verlag: Berlin, 1980; Baeckvall, J. E. Pure Appl. Chem. 1983, 55, 1669. Heck, R. H. Palladium Reagents for Organic Synthesis; Academic Press: New York, 1985. Oppolzer, W. Angew. Chem. 1989, 101, 39. Trost, B. M. Acc. Chem. Res. 1990, 23, 34. Larock, R. C. Adv. Met.-Org. Chem. 1994, 3, 97.
2. For representative reviews, see: Trost, B. M. Tetrahedron 1977, 33, 2615. Tsuji, J. Top. Curr. Chem. 1980, 91, 29. Kumada, M. Pure Appl. Chem. 1980, 52, 669. Negishi, E. I. Acc. Chem. Res. 1982, 15, 340. Tsuji, J. Organic Synthesis with Palladium Compounds; Springer-Verlag: Berlin, 1980; Baeckvall, J. E. Pure Appl. Chem. 1983, 55, 1669. Heck, R. H. Palladium Reagents for Organic Synthesis; Academic Press: New York, 1985. Oppolzer, W. Angew. Chem. 1989, 101, 39. Trost, B. M. Acc. Chem. Res. 1990, 23, 34. Larock, R. C. Adv. Met.-Org. Chem. 1994, 3, 97.
3. For representative reviews, see: Trost, B. M. Tetrahedron 1977, 33, 2615. Tsuji, J. Top. Curr. Chem. 1980, 91, 29. Kumada, M. Pure Appl. Chem. 1980, 52, 669. Negishi, E. I. Acc. Chem. Res. 1982, 15, 340. Tsuji, J. Organic Synthesis with Palladium Compounds; Springer-Verlag: Berlin, 1980; Baeckvall, J. E. Pure Appl. Chem. 1983, 55, 1669. Heck, R. H. Palladium Reagents for Organic Synthesis; Academic Press: New York, 1985. Oppolzer, W. Angew. Chem. 1989, 101, 39. Trost, B. M. Acc. Chem. Res. 1990, 23, 34. Larock, R. C. Adv. Met.-Org. Chem. 1994, 3, 97.
4. For representative reviews, see: Trost, B. M. Tetrahedron 1977, 33, 2615. Tsuji, J. Top. Curr. Chem. 1980, 91, 29. Kumada, M. Pure Appl. Chem. 1980, 52, 669. Negishi, E. I. Acc. Chem. Res. 1982, 15, 340. Tsuji, J. Organic Synthesis with Palladium Compounds; Springer-Verlag: Berlin, 1980; Baeckvall, J. E. Pure Appl. Chem. 1983, 55, 1669. Heck, R. H. Palladium Reagents for Organic Synthesis; Academic Press: New York, 1985. Oppolzer, W. Angew. Chem. 1989, 101, 39. Trost, B. M. Acc. Chem. Res. 1990, 23, 34. Larock, R. C. Adv. Met.-Org. Chem. 1994, 3, 97.
5. For representative reviews, see: Trost, B. M. Tetrahedron 1977, 33, 2615. Tsuji, J. Top. Curr. Chem. 1980, 91, 29. Kumada, M. Pure Appl. Chem. 1980, 52, 669. Negishi, E. I. Acc. Chem. Res. 1982, 15, 340. Tsuji, J. Organic Synthesis with Palladium Compounds; Springer-Verlag: Berlin, 1980; Baeckvall, J. E. Pure Appl. Chem. 1983, 55, 1669. Heck, R. H. Palladium Reagents for Organic Synthesis; Academic Press: New York, 1985. Oppolzer, W. Angew. Chem. 1989, 101, 39. Trost, B. M. Acc. Chem. Res. 1990, 23, 34. Larock, R. C. Adv. Met.-Org. Chem. 1994, 3, 97.
6. For representative reviews, see: Trost, B. M. Tetrahedron 1977, 33, 2615. Tsuji, J. Top. Curr. Chem. 1980, 91, 29. Kumada, M. Pure Appl. Chem. 1980, 52, 669. Negishi, E. I. Acc. Chem. Res. 1982, 15, 340. Tsuji, J. Organic Synthesis with Palladium Compounds; Springer-Verlag: Berlin, 1980; Baeckvall, J. E. Pure Appl. Chem. 1983, 55, 1669. Heck, R. H. Palladium Reagents for Organic Synthesis; Academic Press: New York, 1985. Oppolzer, W. Angew. Chem. 1989, 101, 39. Trost, B. M. Acc. Chem. Res. 1990, 23, 34. Larock, R. C. Adv. Met.-Org. Chem. 1994, 3, 97.
7. For representative reviews, see: Trost, B. M. Tetrahedron 1977, 33, 2615. Tsuji, J. Top. Curr. Chem. 1980, 91, 29. Kumada, M. Pure Appl. Chem. 1980, 52, 669. Negishi, E. I. Acc. Chem. Res. 1982, 15, 340. Tsuji, J. Organic Synthesis with Palladium Compounds; Springer-Verlag: Berlin, 1980; Baeckvall, J. E. Pure Appl. Chem. 1983, 55, 1669. Heck, R. H. Palladium Reagents for Organic Synthesis; Academic Press: New York, 1985. Oppolzer, W. Angew. Chem. 1989, 101, 39. Trost, B. M. Acc. Chem. Res. 1990, 23, 34. Larock, R. C. Adv. Met.-Org. Chem. 1994, 3, 97.
8. For representative reviews, see: Trost, B. M. Tetrahedron 1977, 33, 2615. Tsuji, J. Top. Curr. Chem. 1980, 91, 29. Kumada, M. Pure Appl. Chem. 1980, 52, 669. Negishi, E. I. Acc. Chem. Res. 1982, 15, 340. Tsuji, J. Organic Synthesis with Palladium Compounds; Springer-Verlag: Berlin, 1980; Baeckvall, J. E. Pure Appl. Chem. 1983, 55, 1669. Heck, R. H. Palladium Reagents for Organic Synthesis; Academic Press: New York, 1985. Oppolzer, W. Angew. Chem. 1989, 101, 39. Trost, B. M. Acc. Chem. Res. 1990, 23, 34. Larock, R. C. Adv. Met.-Org. Chem. 1994, 3, 97.
9. For representative reviews, see: Trost, B. M. Tetrahedron 1977, 33, 2615. Tsuji, J. Top. Curr. Chem. 1980, 91, 29. Kumada, M. Pure Appl. Chem. 1980, 52, 669. Negishi, E. I. Acc. Chem. Res. 1982, 15, 340. Tsuji, J. Organic Synthesis with Palladium Compounds; Springer-Verlag: Berlin, 1980; Baeckvall, J. E. Pure Appl. Chem. 1983, 55, 1669. Heck, R. H. Palladium Reagents for Organic Synthesis; Academic Press: New York, 1985. Oppolzer, W. Angew. Chem. 1989, 101, 39. Trost, B. M. Acc. Chem. Res. 1990, 23, 34. Larock, R. C. Adv. Met.-Org. Chem. 1994, 3, 97.
10. For representative reviews, see: Trost, B. M. Tetrahedron 1977, 33, 2615. Tsuji, J. Top. Curr. Chem. 1980, 91, 29. Kumada, M. Pure Appl. Chem. 1980, 52, 669. Negishi, E. I. Acc. Chem. Res. 1982, 15, 340. Tsuji, J. Organic Synthesis with Palladium Compounds; Springer-Verlag: Berlin, 1980; Baeckvall, J. E. Pure Appl. Chem. 1983, 55, 1669. Heck, R. H. Palladium Reagents for Organic Synthesis; Academic Press: New York, 1985. Oppolzer, W. Angew. Chem. 1989, 101, 39. Trost, B. M. Acc. Chem. Res. 1990, 23, 34. Larock, R. C. Adv. Met.-Org. Chem. 1994, 3, 97.
11. For representative reviews, see: Trost, B. M. Acc. Chem. Res. 1980, 13, 385.
12. For representative reviews, see: Stille, J. F. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
13. For representative reviews, see: Heck, R. H. Acc. Chem. Res. 1979, 12, 146. Overman, L. E. Pure Appl. Chem. 1994, 66, 1423.
14. For representative reviews, see: Heck, R. H. Acc. Chem. Res. 1979, 12, 146. Overman, L. E. Pure Appl. Chem. 1994, 66, 1423.
15. For a representative review, see: Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
16. For a representative review, see: Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991.
17. Li, C. J. Chem. Rev. 1992, 92, 2023. Li, C. J.; Chan, T. H. Organic Reaction in Aqueous Media; John Wiley & Sons: New York, 1997. See also: Organic Synthesis in Water; Grieco, P. A., Ed.; Thomson Science: Glasgow, 1998.
18. Li, C. J. Chem. Rev. 1992, 92, 2023. Li, C. J.; Chan, T. H. Organic Reaction in Aqueous Media; John Wiley & Sons: New York, 1997. See also: Organic Synthesis in Water; Grieco, P. A., Ed.; Thomson Science: Glasgow, 1998.
19. Li, C. J. Chem. Rev. 1992, 92, 2023. Li, C. J.; Chan, T. H. Organic Reaction in Aqueous Media; John Wiley & Sons: New York, 1997. See also: Organic Synthesis in Water; Grieco, P. A., Ed.; Thomson Science: Glasgow, 1998.
20. After initial submission this work, an air-stable and polymer-supported palladium-catalyzed Suzuki reaction was reported, see: Zhang, T. Y.; Allen, M. J. Tetrahedron Lett. 1999, 40, 5813. For a Heck-type reaction with arenediazonium salts, see: Brunner, H.; Le Cousturier de Courcy, N.; Genet, J.-P. Tetrahedron Lett. 1999, 40, 4815.
21. After initial submission this work, an air-stable and polymer-supported palladium-catalyzed Suzuki reaction was reported, see: Zhang, T. Y.; Allen, M. J. Tetrahedron Lett. 1999, 40, 5813. For a Heck-type reaction with arenediazonium salts, see: Brunner, H.; Le Cousturier de Courcy, N.; Genet, J.-P. Tetrahedron Lett. 1999, 40, 4815.
22. For representative reviews, see: Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977. Sainsbury, M. Tetrahedron 1980, 36, 3327.
23. For representative reviews, see: Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977. Sainsbury, M. Tetrahedron 1980, 36, 3327.
24. For representative reviews, see: Fanta, P. E. Chem. Rev. 1946, 38, 139; 1964, 64, 613; Synthesis 1974, 9. Goshaev, M.; Otroshchenko, O. S.; Sadykov, A. S. Russ. Chem. Soc. Rev. 1972, 41, 1046. See also: Posner, G. H. An Introduction to Synthesis Using Organocopper Reagents; John Wiley: New York, 1980. Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655.
25. For representative reviews, see: Fanta, P. E. Chem. Rev. 1946, 38, 139; 1964, 64, 613; Synthesis 1974, 9. Goshaev, M.; Otroshchenko, O. S.; Sadykov, A. S. Russ. Chem. Soc. Rev. 1972, 41, 1046. See also: Posner, G. H. An Introduction to Synthesis Using Organocopper Reagents; John Wiley: New York, 1980. Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655.
26. For representative reviews, see: Fanta, P. E. Chem. Rev. 1946, 38, 139; 1964, 64, 613; Synthesis 1974, 9. Goshaev, M.; Otroshchenko, O. S.; Sadykov, A. S. Russ. Chem. Soc. Rev. 1972, 41, 1046. See also: Posner, G. H. An Introduction to Synthesis Using Organocopper Reagents; John Wiley: New York, 1980. Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655.
27. For representative reviews, see: Fanta, P. E. Chem. Rev. 1946, 38, 139; 1964, 64, 613; Synthesis 1974, 9. Goshaev, M.; Otroshchenko, O. S.; Sadykov, A. S. Russ. Chem. Soc. Rev. 1972, 41, 1046. See also: Posner, G. H. An Introduction to Synthesis Using Organocopper Reagents; John Wiley: New York, 1980. Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655.
28. For representative reviews, see: Fanta, P. E. Chem. Rev. 1946, 38, 139; 1964, 64, 613; Synthesis 1974, 9. Goshaev, M.; Otroshchenko, O. S.; Sadykov, A. S. Russ. Chem. Soc. Rev. 1972, 41, 1046. See also: Posner, G. H. An Introduction to Synthesis Using Organocopper Reagents; John Wiley: New York, 1980. Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655.
29. For representative reviews, see: Fanta, P. E. Chem. Rev. 1946, 38, 139; 1964, 64, 613; Synthesis 1974, 9. Goshaev, M.; Otroshchenko, O. S.; Sadykov, A. S. Russ. Chem. Soc. Rev. 1972, 41, 1046. See also: Posner, G. H. An Introduction to Synthesis Using Organocopper Reagents; John Wiley: New York, 1980. Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655.
30. For Ni-catalyzed Ullman-type couplings, see: Takagi, Hayama, Sasaki. Bull. Chem. Soc. Jpn 1984, 57, 1887. Meyer, Rollin, Perchon. J. Organomet. Chem. 1987, 333, 263.
31. For Ni-catalyzed Ullman-type couplings, see: Takagi, Hayama, Sasaki. Bull. Chem. Soc. Jpn 1984, 57, 1887. Meyer, Rollin, Perchon. J. Organomet. Chem. 1987, 333, 263.
32. Recently, Liebeskind reported an ambient temperature Ullmann-type coupling, see: Zhang, S.; Zhang, D.; Liebeskind, L. S. J. Org. Chem. 1997, 62, 2312 and references cited therein.
33. Previously, Pd/C was used as the catalyst for Ullmann-type coupling with moderate yields under phase-transfer conditions by refluxing at 100 °C, see: Bamfield, P.; Quan, P. M. Synthesis 1978, 537.
34. Representative Experimental Procedure: A mixture of Pd/C (80 mg, 10%) and zinc powder (80 mg, 1.2 mmol) in 4 mL of water/acetone (1:1) was stirred at ambient temperature under an atmosphere of air for 30 min. To the mixture was added p-iodoanisole (100 mg, 0.4 mmol), and the stirring was continued overnight under this same reaction conditions. The reaction mixture was extracted with ether. GC/MS analysis of the reaction mixture revealed two components with 4,4′-dimethoxybiphenyl (92%) and anisole (8%).
35. For representative examples, see: Tour, J. Chem. Rev. 1996, 96, 537. Brase, S.; De Meijere, A. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH Verlag: Weiheim, 1998; Baughman, R. H.; Bredas, J. L.; Chance, R. R.; Elsenbaumer, R. L.; Shacklette, L. W. Chem. Rev. 1982, 82, 209.
36. For representative examples, see: Tour, J. Chem. Rev. 1996, 96, 537. Brase, S.; De Meijere, A. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH Verlag: Weiheim, 1998; Baughman, R. H.; Bredas, J. L.; Chance, R. R.; Elsenbaumer, R. L.; Shacklette, L. W. Chem. Rev. 1982, 82, 209.
37. For representative examples, see: Tour, J. Chem. Rev. 1996, 96, 537. Brase, S.; De Meijere, A. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH Verlag: Weiheim, 1998; Baughman, R. H.; Bredas, J. L.; Chance, R. R.; Elsenbaumer, R. L.; Shacklette, L. W. Chem. Rev. 1982, 82, 209.