Novel and general cross-coupling reactions of alkynylzinc reagents and organotellurium compounds

Tetrahedron Letters

Volumn 41, Issue 4, 2000, Pages 437-440

  Dabdoub, Miguel J ^a   Dabdoub, Vânia B ^b   Marino, Joseph P ^b  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOTELLURIUM DERIVATIVE; ZINC DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; SYNTHESIS;

EID: 0034700774     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02088-2     Document Type: Article

References (28)

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2. b) Knochel, P.; Singer, R. D. Chem Rev. 1993, 93, 2117.
3. c) Erdik, E. Organozinc Reagents in Organic Synthesis; CRC Press, Inc. Boca Raton, Florida, 1996.
4. d) Uchiyama, M.; Kameda, M.; Mishima, O.; Yokoyama, N.; Koike, M.; Kondo, Y.; Sakamoto, T. J. Am. Chem. Soc. 1998, 120, 4934.
5. 2: a) King, A. O.; Okukado, N.; Negishi, E. J. Chem. Soc. Chem. Commun. 1977, 683. b) King, A. O.; Negishi, E. J. Org. Chem. 1978, 43, 358. c) Negishi, E.; Akiyashi, K.; Takahashi, T, J. Chem. Soc. Chem. Commun. 1987, 477. d) Abarbri, M.; Parrain, J.-L.; Cintrat, J.-C.; Duchene, A. Synthesis 1996, 82. e) Rossi, R.; Bellina, F.; Carpita, A.; Gori, R. Synlett 1995, 344.
6. 2: a) King, A. O.; Okukado, N.; Negishi, E. J. Chem. Soc. Chem. Commun. 1977, 683. b) King, A. O.; Negishi, E. J. Org. Chem. 1978, 43, 358. c) Negishi, E.; Akiyashi, K.; Takahashi, T, J. Chem. Soc. Chem. Commun. 1987, 477. d) Abarbri, M.; Parrain, J.-L.; Cintrat, J.-C.; Duchene, A. Synthesis 1996, 82. e) Rossi, R.; Bellina, F.; Carpita, A.; Gori, R. Synlett 1995, 344.
7. 2: a) King, A. O.; Okukado, N.; Negishi, E. J. Chem. Soc. Chem. Commun. 1977, 683. b) King, A. O.; Negishi, E. J. Org. Chem. 1978, 43, 358. c) Negishi, E.; Akiyashi, K.; Takahashi, T, J. Chem. Soc. Chem. Commun. 1987, 477. d) Abarbri, M.; Parrain, J.-L.; Cintrat, J.-C.; Duchene, A. Synthesis 1996, 82. e) Rossi, R.; Bellina, F.; Carpita, A.; Gori, R. Synlett 1995, 344.
8. 2: a) King, A. O.; Okukado, N.; Negishi, E. J. Chem. Soc. Chem. Commun. 1977, 683. b) King, A. O.; Negishi, E. J. Org. Chem. 1978, 43, 358. c) Negishi, E.; Akiyashi, K.; Takahashi, T, J. Chem. Soc. Chem. Commun. 1987, 477. d) Abarbri, M.; Parrain, J.-L.; Cintrat, J.-C.; Duchene, A. Synthesis 1996, 82. e) Rossi, R.; Bellina, F.; Carpita, A.; Gori, R. Synlett 1995, 344.
9. 2: a) King, A. O.; Okukado, N.; Negishi, E. J. Chem. Soc. Chem. Commun. 1977, 683. b) King, A. O.; Negishi, E. J. Org. Chem. 1978, 43, 358. c) Negishi, E.; Akiyashi, K.; Takahashi, T, J. Chem. Soc. Chem. Commun. 1987, 477. d) Abarbri, M.; Parrain, J.-L.; Cintrat, J.-C.; Duchene, A. Synthesis 1996, 82. e) Rossi, R.; Bellina, F.; Carpita, A.; Gori, R. Synlett 1995, 344.
10. Few examples of alkyl(aryl)mono-(1-alkynyl) or di(1-alkynyl) zinc reagents are known and were prepared by the direct metallation of 1-alkynes with organozinc reagents under hard reactional conditions: a) Okhlobystin, O. Y.; Zakharkin, L. I. J. Organometal. Chem. 1965, 3, 257. b) Jeffery, E. A.; Mole, T. J. Organometal. Chem. 1968, 11, 393. c) Nast, R.; Künzel, O.; Müller, R. Chem. Ber. 1962, 95, 2155. d) Niwa, S.; Soai, K. J. Chem. Soc. Perkin Trans. 1 1990, 937.
11. Few examples of alkyl(aryl)mono-(1-alkynyl) or di(1-alkynyl) zinc reagents are known and were prepared by the direct metallation of 1-alkynes with organozinc reagents under hard reactional conditions: a) Okhlobystin, O. Y.; Zakharkin, L. I. J. Organometal. Chem. 1965, 3, 257. b) Jeffery, E. A.; Mole, T. J. Organometal. Chem. 1968, 11, 393. c) Nast, R.; Künzel, O.; Müller, R. Chem. Ber. 1962, 95, 2155. d) Niwa, S.; Soai, K. J. Chem. Soc. Perkin Trans. 1 1990, 937.
12. Few examples of alkyl(aryl)mono-(1-alkynyl) or di(1-alkynyl) zinc reagents are known and were prepared by the direct metallation of 1-alkynes with organozinc reagents under hard reactional conditions: a) Okhlobystin, O. Y.; Zakharkin, L. I. J. Organometal. Chem. 1965, 3, 257. b) Jeffery, E. A.; Mole, T. J. Organometal. Chem. 1968, 11, 393. c) Nast, R.; Künzel, O.; Müller, R. Chem. Ber. 1962, 95, 2155. d) Niwa, S.; Soai, K. J. Chem. Soc. Perkin Trans. 1 1990, 937.
13. Few examples of alkyl(aryl)mono-(1-alkynyl) or di(1-alkynyl) zinc reagents are known and were prepared by the direct metallation of 1-alkynes with organozinc reagents under hard reactional conditions: a) Okhlobystin, O. Y.; Zakharkin, L. I. J. Organometal. Chem. 1965, 3, 257. b) Jeffery, E. A.; Mole, T. J. Organometal. Chem. 1968, 11, 393. c) Nast, R.; Künzel, O.; Müller, R. Chem. Ber. 1962, 95, 2155. d) Niwa, S.; Soai, K. J. Chem. Soc. Perkin Trans. 1 1990, 937.
14. sp2-Te: Dabdoub, M. J.; Comasseto, J. V. Organometallics 1989, 7, 84.
15. a) Dabdoub, M. J.; Cassol, T. M. Tetrahedron 1995, 51, 12971.
16. b) Dabdoub, M. J.; Begnini, M. L.; Cassol, T. M.; Guerrero Jr., P. G.; Silveira, C. C. Tetrahedron Lett. 1995, 36, 7623.
17. c) Barros, S. M.; Dabdoub, M. J.; Dabdoub, V. B.; Comasseto, J. V. Organometallics 1989, 8, 1661.
18. a) Dabdoub, M. J.; Dabdoub, V. B. Tetrahedron 1995, 51, 9839.
19. b) Dabdoub, M. J.; Dabdoub, V. B.; Pereira, M. A.; Zukerman-Schpector, J. J. Org. Chem. 1996, 61, 9503.
20. c) Dabdoub, M. J.; Justino, A.; Guerrero Jr., P. G.; Zukerman-Schpector, J. Organometallics 1998, 17, 1901.
21. a) Engman, L. Organometallics, 1986, 5, 427.
22. b) Petragnani, N. In Comprehensive Organometallic Chemistry II; McKillop, A., Ed.; Pergamon, 1995; Volume 11, pp. 571-602.
23. The cross-coupling reaction of aryl iodides with other alkynylzinc reagents (RC≡CZnX) was previously described; see Ref. 2b in the present paper, see also: Negishi, E. Acc. Chem. Res. 1982, 15, 340.
24. 2 (0.408 g, 3.0 mmol) to a solution of a lithium acetylide generated by treating a terminal alkyne (6.0 mmol) in THF at 0°C with BuLi (6.0 mmol). After stirring for 20 min at rt, compounds 3 were used in situ.
25. Selected reviews: a) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. b) Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453. c) Enediynes Antibiotics as Antitumor Agents; Doyle, T. W., Borders, D. B., Eds.; Marcel Dekker: New York, 1994. d) DNA and RNA Cleavers and Chemotherapy of Cancer and Viral Diseases; Meunier, B., Ed.; Kluwer Academic Publishers: Dordrecht, 1996; pp. 1-73.
26. Selected reviews: a) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. b) Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453. c) Enediynes Antibiotics as Antitumor Agents; Doyle, T. W., Borders, D. B., Eds.; Marcel Dekker: New York, 1994. d) DNA and RNA Cleavers and Chemotherapy of Cancer and Viral Diseases; Meunier, B., Ed.; Kluwer Academic Publishers: Dordrecht, 1996; pp. 1-73.
27. Selected reviews: a) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. b) Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453. c) Enediynes Antibiotics as Antitumor Agents; Doyle, T. W., Borders, D. B., Eds.; Marcel Dekker: New York, 1994. d) DNA and RNA Cleavers and Chemotherapy of Cancer and Viral Diseases; Meunier, B., Ed.; Kluwer Academic Publishers: Dordrecht, 1996; pp. 1-73.
28. Selected reviews: a) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. b) Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453. c) Enediynes Antibiotics as Antitumor Agents; Doyle, T. W., Borders, D. B., Eds.; Marcel Dekker: New York, 1994. d) DNA and RNA Cleavers and Chemotherapy of Cancer and Viral Diseases; Meunier, B., Ed.; Kluwer Academic Publishers: Dordrecht, 1996; pp. 1-73.