An efficient ligand exchange reaction of (e)-[β- (trifluoromethanesulfonyloxy)ethenyl](phenyl)iodonium triflates with aryl- and alkynyllithium reagents leading to diaryl- and alkynyliodonium triflates

Synthesis

Volumn , Issue 1, 2000, Pages 81-83

  Pirguliyev, Namig Sh ^a   Brel, Valery K ^b   Akhmedov, Navruz G ^a   Zefirov, Nikolai S ^a,b  

^a MOSCOW STATE UNIVERSITY   (Russian Federation)

^b INSTITUTE OF PHYSIOLOGICALLY ACTIVE COMPOUNDS   (Russian Federation)

Author keywords

Alkynes; Aryl halides; Hypervalent elements; Iodine

Indexed keywords

TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; CHEMICAL REACTION; SYNTHESIS; TECHNIQUE;

EID: 0033959232     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2000-6234     Document Type: Article

References (31)

1. (a) Koser, G. F. In The Chemistry of Functional Groups, Supplement D; Patai, S.; Rappoport, Z., Eds.; Wiley: New York, 1983; Chap. 18, p. 721 and Chap. 25 p. 1265.
2. (b) Varvoglis, A. Synthesis 1984, 709.
3. (c) Moriarty, R. M.; Prakash, O. Acc. Chem. Res. 1986, 19, 244.
4. (d) Ochiai, M.; Nagao, Y. Yuki GoseiKagaku Kyokaishi 1986, 44, 660.
5. (e) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH: New York, 1992.
6. f) Stang, P. J. Angew. Chem. Int. Ed. Engl. 1992, 31, 274.
7. (a) Sandin, R. B. Chem. Rev. 1943, 32, 249.
8. (b) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123.
9. Zhdankin, V. V.; Stang, P. J. Tetrahedron 1998, 54, 10927.
10. (a) Kitamura, T.; Kotani, M.; Fujiwara, Y. Tetrahedron Lett. 1996, 57, 3721.
11. (b) Kitamura, T.; Matsuyuki, J.; Nagata, K.; Furuki, R., Taniguchi, H. Synthesis 1992, 945.
12. (c) Stang, P. J.; Zhdankin, V. V.; Tykwinski; R., Zefirov, N. S. Tetrahedron Lett. 1991, 32, 7497.
13. For reviews see: (a) Huang, W.-Y.; Chen, Q.-Y. In The Chemistry of Sulfonic Acids, Esters and their Derivatives; Patai, S.; Rappoport, Z., Eds.;Wiley-Interscience: Chichester 1991; Chap. 21, p.903.
14. (b) Moriarty, R. M.; Vaide, R. K. Synthesis 1990, 431.
15. (c) Stang, P. J.; White, M. R. Aldrichimica Acta 1983, 16, 15.
16. (d) Howells, R. D.; Mc Cown, J. D. Chem. Rev. 1977, 77, 69.
17. (e) Stang, P. J.; Hanack, M.; Subramanian, L. R. Synthesis 1982, 85.
18. (a) Freidlina, R. Kh.; Brainina, E. M.; Nesmeyanov, A. N. Bull Acad. Sci. URSS. Classe Sci. Chim. 1945, 647; Chem. Abstr. 1946, 40, 4686.
19. (a) Freidlina, R. Kh.; Brainina, E. M.; Nesmeyanov, A. N. Bull Acad. Sci. URSS. Classe Sci. Chim. 1945, 647; Chem. Abstr. 1946, 40, 4686.
20. (b) Brainina, E. M.; Freidlina, R. Kh. Bull. Acad. Sci. URSS. Classe Sci. Chim. 1947, 623; Chem. Abstr. 1948, 42, 5863a.
21. (b) Brainina, E. M.; Freidlina, R. Kh. Bull. Acad. Sci. URSS. Classe Sci. Chim. 1947, 623; Chem. Abstr. 1948, 42, 5863a.
22. Oae, S.; Uchida, Y. Acc. Chem. Res. 1991, 24, 202.
23. (a) Beringer, F. M.; Nathan, R. A. J. Org. Chem. 1970, 35, 2095.
24. (b) Gronowitz, S.; Ander, I. Acta. Chem. Scand. 1975, B29, 513.
25. Gronowitz, S., Holm, B. J. Heterocycl. Chem. 1977, 14, 281.
26. Margida, A. J.; Koser, G. F. J. Org. Chem. 1984, 49, 4703.
27. (e) Kitamura, T.; Kotani, M.; Fujiwara, Y. Tetrahedron Lett. 1996, 37, 3721.
28. Kasumov, T. M.; Pirguliyev, N. Sh.; Brel, V. K.; Grishin, Yu. K.; Zefirov, N. S.; Stang, P. J. Tetrahedron 1997, 53, 13139.
29. Williamson, B. L.; Stang, P. J.; Arif, A. M. J. Am. Chem. Soc. 1993, 115, 2590.
30. Bachi, M. D.; Bar-Ner, N.; Critell, Ch. M.; Stang, P. J.; Williamson, B. L. J. Org. Chem. 1991, 56, 3912.
31. Perrin, D. D.; Armarego, W. L. F.; Perrin, D. R. Purification of Laboratiry chemicals; Pergamon: 1988.