Palladium-Catalyzed Coupling of sp2-Hybridized Tellurides

Accounts of Chemical Research

Volumn 36, Issue 10, 2003, Pages 731-738

  Zeni, Gilson ^a   Braga, Antonio L ^a   Stefani, Hélio A ^b  

^a FEDERAL UNIVERSITY OF SANTA MARIA   (Brazil)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

CATION; PALLADIUM; TELLURIUM;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS REACTION; HYBRIDIZATION; STEREOCHEMISTRY; STEREOISOMERISM;

EID: 0142151158     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar0202621     Document Type: Article

References (61)

1. (a) Comasseto, J. V.; Barrientos-Astigarraga, R. E. Add a Little Tellurium to your Synthetic Plans! Aldrichim. Acta 2000, 33, 66-78.
2. (b) Comasseto, J. V.; Ling, L. W.; Petragnani, N.; Stefani, H. A. Vinylic Selenides and Tellurides - Preparation, Reactivity and Synthetic Applications. Synthesis 1997, 4, 373-403.
3. (c) Petragnani, N. Tellurium in Organic Synthesis; Academic Press: London, 1994.
4. (a) Barros, S. M.; Dabdoub, M. J.; Dabdoub, V. B.; Comasseto, J. V. Hydrotelluration of Acetylenes - Synthesis of Vinylic Tellurides, Divinyl Tellurides, and 1-(Organyltelluro)-1,3-Butadienes. Organometallics 1989, 8, 1661-1665.
5. (b) Zeni, G.; Formiga, H. B.; Comasseto, J. V. Improved Procedure for the Hydrotelluration of Alkynes. Tetrahedron Lett. 2000, 41, 1311-1313.
6. Dabdoub, M. J.; Cassol, T. M. Total Control on the Synthesis of Regio and Stereoisomerrs of Vinylic Tellurides. Tetrahedron 1995, 51, 12971-12982.
7. (a) Chieffi, A.; Comasseto, J. V. The Coupling Reaction Between Vinylic Tellurides and Lower Order Cyanocuprates. Synlett 1995, 671-674.
8. (b) Marino, J. P.; McClure, M. S.; Holub, D. P.; Comasseto, J. V.; Tucci, F. C. Stereocontrolled Synthesis of (-)-Macrolactin A. J. Am. Chem. Soc. 2002, 124, 1664-1668.
9. Barros, S. M.; Comasseto, J. V.; Barriel, J. N. Vinyllithiums from Butyl-vinyl Tellurides and bis-Vinyl Tellurides. Tetrahedron Lett. 1989, 30, 7353-7356.
10. Hirro, T.; Kambe, N.; Ogawa, A.; Miyoshi, N.; Murai, S.; Sonoda, N. Lithium-tellurium Exchange-A New Entry to Organolithium Compounds. Angew. Chem., Int. Ed. Engl. 1987, 11, 1187-1188.
11. Marino, J. P.; Tucci, F. C.; Comasseto, J. V. An Efficient Preparation of Functionalized Z-Vinylcuprates from Terminal Acetylenes and Their Reactions with Epoxides. Synlett 1993, 761-763.
12. Sonogashira, K.; Tohda, Y.; Hagihara, N. Convenient Synthesis of Acetylenes-Catalytic Substitutions of Acetylenic Hydrogen with Bromoalkenes, Iodoarenes, and Bromopyridines. Tetrahedron Lett. 1975, 4467-4470.
13. Dieck, H. A.; Heck, F. R. Palladium Catalyzed Synthesis of Aryl, Heterocyclic and Vinylic Acetylene Derivatives. J. Organomet. Chem. 1975, 93, 259-263.
14. Suzuki, A. Organoboron Compounds in New Synthetic Reactions. Pure Appl. Chem. 1985, 57, 1749-1758.
15. Scott, W. J.; Peña, M. R.; Sward, K.; Stoessel, S. J.; Stille, J. K. Palladium-Catalyzed Olefination of Vinyl Triflates. J. Org. Chem. 1985, 50, 2302-2308.
16. International Symposium on 30 Years of the Cross-Coupling Reaction, J. Organomet. Chem. 2002, 653, 1-303.
17. Zeni G.; Panatieri, R. B.; Lissner, E.; Menezes, P. H.; Braga, A. L.; Stefani, H. A. Synthesis of Polyacetylenic Acids Isolated from Heisteria Acuminata Org. Lett. 2001, 6, 819-821.
18. Uemura, S.; Wakasugi, M.; Okano, M. Carbodetelluration of Aryltellurium(IV) Compounds-Olefin Arylation and Aromatic Coupling. J. Organomet. Chem. 1980, 194, 277-283.
19. Nishibayashi, Y.; Cho, S. C.; Uemura, S. Palladium-Catalyzed Cross-Coupling Reactions Between Organic Tellurides and Alkenes. J. Organomet. Chem. 1996, 507, 197-200.
20. Nishibayashi, Y.; Cho, S. C.; Ohe, K.; Uemura, S. Palladium-Catalyzed Homocoupling Reactions of Organic Tellurides. J. Organomet. Chem. 1996, 526, 335-339.
21. Kang, S.-K.; Lee, S.-W.; Ryu, H.-C. Palladium- and Copper-Catalyzed Cross-Coupling and Carbonylative Cross-Coupling of Organotellurium Compounds with Organostannanes. Chem. Commun. 1999, 2117-2118.
22. Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chem. Rev. 1995, 95, 2457-2483.
23. Kang, S.-K.; Hong, Y.-T.; Kim, D.-H.; Lee, S.-H. Palladium-Catalysed Cross-Coupling of Organotellurium Compounds with Organoboronic Acids. J. Chem. Res. 2001, 283-285.
24. Kang, S.-K.; Lee, S.-W.; Kim, M.-S.; Kwon, H.-S. Palladium-Catalyzed Cross-Coupling of Organotellurium Compounds with Hypervalent Iodonium Salts. Synth. Commun. 2001, 11, 1721-1725.
25. Grissom J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. The Chemistry of Enediynes, Enyne, Allenes and Related Compounds. Tetrahedron 1996, 52, 6453-6518.
26. Tamao, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; pp 435-480.
27. (a) Alami, M.; Linstrumelle, G. AN Efficient Palladium-Catalyzed Reaction of Vinyl Chlorides with Terminal Acetylenes. Tetrahedron Lett. 1991, 32, 6109-6112.
28. (b) Alami, M.; Peyrat, J.-F.; Brion, J.-D. 1,2-Dihalogenoalkenes: Useful Linchpins to Unsaturated Compounds via Palladium or Nickel Catalysis. Synthesis 2000, 1499-1518.
29. (c) Dieck, H. A.; Heck, F. R. Palladium Catalyzed Synthesis of Aryl, Heterocyclic and Vinylic Acetylene Derivatives. J. Organomet. Chem. 1975, 93, 259-263.
30. 2 in Piperidine: Versatile Catalysts for Sonogashira Reaction of Vinyl Chlorides at Room Temperature. J. Organomet. Chem. 2001, 624, 114-123.
31. Miyaura, N.; Yamada, K.; Suginome, H.; Suzuki, A. Novel and Convenient Method for the Stereospecific and Regiospecific Synthesis of Conjugated Alkadienes and Alkenynes via the Palladium-Catalised Cross-Coupling Reaction of 1-Alkenylboranes with Bromoalkenes and Bromoalkynes. J. Am. Chem. Soc. 1985, 107, 972-980.
32. (a) Normant, J. F.; Commerçon, A.; Villièras, J. Synthesis of Enynes and Conjugated Dienes Using Organocuprous Vinyl-Application to Synthesis of Bombykol. Tetrahedron Lett. 1975, 1465-1468.
33. (b) Alexakis, A.; Cahiez, G.; Normant, J. F. Vinyl-Copper Derivatives 10. Alkylation of (Z)-Dialkenylcuprates. Synthesis 1979, 826-830.
34. Magriotis, P. A.; Scott, M. E.; Kim, K. D. A Novel Approach to the Synthesis of Enediynes. Tetrahedron Lett. 1991, 32, 6085-6088.
35. Negishi, E. I.; Okukado, N.; King, A. O.; Van Horn, D. E.; Spiegel, B. I. Selective Carbon-Carbon Bond Formation via Transition-Metal Catalysis. 8. Double Metal Catalysis in Cross-Coupling Reaction and its Application to Stereo-Selective and Regioselective Synthesis of Trisubstituted Olefins. J. Am. Chem. Soc. 1978, 100, 2254-2256.
36. Dang, H. P.; Linstrumelle, G. Efficient Stereospecific Synthesis of Olefins by Palladium-Catalyzed Reaction of Reagents with Alkenyl Iodides. Tetrahedron Lett. 1978, 2,191-194.
37. Dabdoub, M. J.; Dabdoub, V. B. Highly Chemoselective Triple Bond Reductions on Unsymmetrical 1,4-Diorganyl-1,3-Butadiynes. Tetrahedron 1995, 51, 9839-9850.
38. (a) Barrientos-Astigarraga, R. E.; Moraes, D. N.; Comasseto, J. V. Highly Unsaturated Conjugated Systems from Vinytic Tellurides. Tetrahedron Lett. 1999, 40, 265-268.
39. (b) De Araujo, M. A.; Comasseto, J. V. Stereoselective and Convergent Route to Z-Enynes and Z-Trisubstituted Enediynes. Synlett 1995, 1145-147.
40. 2/Cul: Synthesis of Z-Enynes and Z-Enediynes. Tetrahedron Lett. 1999, 40, 4619-4622.
41. Tucci, F. C.; Chieffi, A.; Comasseto, J. V.; Marino, J. P. Tellurium in Organic Synthesis. Preparation of Z-Vinylic Cuprates from Z-Vinylic Tellurides and their Reaction with Enones and Epoxides. J. Org. Chem. 1996, 61, 4975-4989.
42. Zeni, G.; Menezes, P. H.; Moro, A. V.; Braga, A. L.; Silveira, C. C.; Stefani, H. A. Stereoselective Synthesis of (Z)-Enynes via Pd(II)/ Cul(I)-catalyzed Cross-coupling Reaction of bis-Vinylic Tellurides with 1-Alkynes. Synlett 2001, 9, 1473-1475.
43. Bakker, J.; Gommers, F. J.; Nieuwenhuis, I.; Wynberg, H. Photoactivation of the Nematocidal Compound alpha-Terthienyl from Roots of Marigolds (Tagetes Species)-Possible Singlet Oxygen Role. J. Biol. Chem. 1979, 254, 1841-1844.
44. Iyengar, S.; Arnason, J. T.; Philogene, B. J. R.; Murand, P.; Werstink, N. H.; Timmins, G. Toxicokinetics of the Phototoxic Allelochemical alpha-Terthienyl in 3 Herbivorous Lepidoptera. Pesticide Biochem. Physiology 1987, 29, 1-9.
45. Matsuura, H.; Saxena, G.; Farmer, S. W.; Hancock, R. E. W.; Towers, G. H. N. An Antibacterial Thiophene from Balsamorhiza sagittata. Planta Med. 1996, 62, 65-66.
46. Chan, G. F. Q.; Towers, G. H. N.; Mitchell, J. C. Ultraviolet-Mediated Antibiotic Activity of Thiophene Compounds of Tagetes. Phytochemistry 1975, 14, 2295-2296.
47. Hudson, J. B.; Graham, E. A.; Miki, N.; Towers, G. H. N.; Hudson L. L.; Rossi, R.; Carpita, A.; Neri, D. Ultraviolet-Mediated Antibiotic-Activity of Synthetic Thiophenes and Their Acetylenic Derivatives. Chemosphere 1989, 18, 2317-2327.
48. Zeni, G.; Nogueira, C. W.; Panatieri, R. B.; Silva, D. O.; Menezes, P. H.; Braga, A. L.; Silveira, C. C.; Stefani, H. A.; Rocha, J. B. T. Synthesis and Anti-inflammatory Activity of Acetylenic Thiophenes. Tetrahedron Lett. 2001, 42, 7921-7923.
49. Gilman, H.; Shirley, D. A. Metalation of Thiophene by Normal-Butyllithium. J. Am. Chem. Soc. 1949, 71, 1870-1871.
50. Winter, C. A.; Risley, E. A.; Nuss, G. W. Carrageenin-Induced Edema in Hind Paw of Rat as an Assay for Antiinflammatory Drugs. Proc. Soc. Exp. Biol. Med. 1962, 111, 544-552.
51. Zeni, G.; Lüdtke, D. S.; Nogueira, C. W.; Panatieri, R. B.; Braga, A. L.; Silveira, C. C.; Stefani, H. A.; Rocha, J. B. T. New Acetylenic Furan Derivatives: Synthesis and Antiinflammatory Activity. Tetrahedron Lett. 2001, 42, 8927-8930.
52. Hilderbrand, R. L.; Henderson, T. O. In The Role of Phosphonates in Living Systems; Hilderbrand, R. L., Ed.; CRC Press: Boca Raton, FL, 1983; pp 5-29.
53. Engel, R. Phosphonates as Analogues of Natural Phosphates. Chem. Rev. 1977, 77, 349-367.
54. Minami, T.; Ichikawa, J.; Nakamura, M.; Okauchi, T.; Kouno, R. Synthesis and Synthetic Utilization of alpha-Functionalized Vinylphosphonates Bearing beta-oxy or beta-thio Substituents. J. Org. Chem. 1998, 63, 6239-6246.
55. Braga, A. L.; de Andrade, L. H.; Silveira, C. C.; Alves, E. F. Stereoselective Addition of Sodium Organyl Chalcogenolates to Alkynylphosphonates: Synthesis of Diethyl 2-(organyl)-2-(organochalcogenyl)vinylphosphonates. Tetrahedron Lett. 2000, 41, 161-163.
56. Braga, A. L.; de Andrade, L. H.; Silveira, C. C.; Moro, A. V.; Zeni, G. Stereospecific Formation of Enynephosphonates via Palladium-Catalyzed Cross-Coupling Reaction of beta-Organotelluro Vinylphosphonates with Alkynes. Tetrahedron Lett. 2001, 42, 8563-8565.
57. Braga, A. L.; Vargas, F.; Zeni, G.; Silveira, C. C.; de Andrade, L. H. Synthesis of beta-Organotelluro Vinylphosphine Oxides by Hydrotelluration of 1-Alkynylphosphine Oxides and Their Palladium-Catalyzed Cross-Coupling with Alkynes. Tetrahedron Lett. 2002, 43, 4399-4402.
58. Zeni, G.; Perin, G.; Cella, R.; Jacob, R. G.; Braga, A. L.; Silveira, C. C.; Stefani, H. A. Synthesis of Cross-Conjugated Geminal Enediynes via Palladium Catalyzed Cross-Coupling Reaction of Ketene Butyltelluroacetals. Synlett 2002, 6, 975-977.
59. (a) Maciel, E. N.; Bolzan, R. C.; Braga, A. L.; Rocha, J. B. T. Diphenyl Diselenide and Diphenyl Ditelluride Differentially Affect δ -Aminolevulinate Dehydratase from Liver, Kidney, and Brain of Mice. J. Biochem. Mol. Toxicol. 2000, 6, 310-319.
60. (b) Nogueira, C. W.; Rotta, L. N.; Perry, M. L.; Souza, D. O.; Rocha, J. B. T. Diphenyl Diselenide and Diphenyl Ditelluride Affect the Rat Glutamatergic System in Vitro and in Vivo. Brain Res. 2001, 906, 157-163.
61. (c) Nogueira, C. W.; Rotta, L. N.; Zeni, G.; Souza, D. O.; Rocha, J. B. T. Exposure to Ebselen Changes Glutamate Uptake and Release by Rat Brain Synaptosomes. Neurochem. Res. 2002, 27, 283-288.