Palladium-catalysed cross-coupling reactions of aryl-, alkenyl- and alkynyl-iodonium salts and iodanes with terminal alkynes in aqueous medium

Chemical Communications

Volumn , Issue 7, 1996, Pages 835-836

  Kang, Suk Ku ^a   Lee, Hong Woo ^a   Jang, Su Bum ^a   Ho, Pil Su ^a  

^a Sungkyunkwan University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002264751     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/cc9960000835     Document Type: Article

References (26)

1. H. A. Dick and F. R. Heck, J. Organomet. Chem., 1975, 93, 259; L. Casar, J. Organomet. Chem., 1975, 93, 253.
2. H. A. Dick and F. R. Heck, J. Organomet. Chem., 1975, 93, 259; L. Casar, J. Organomet. Chem., 1975, 93, 253.
3. K. Sonogashira, Y. Tohda and N. Hagihara, Tetrahedron Lett., 1975, 16, 4467; K. Sonogashira, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 3, p. 521; R. Rossi, A. Carpita and F. Bellina, Org. Prep. Proced. Int., 1995, 27, 129.
4. K. Sonogashira, Y. Tohda and N. Hagihara, Tetrahedron Lett., 1975, 16, 4467; K. Sonogashira, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 3, p. 521; R. Rossi, A. Carpita and F. Bellina, Org. Prep. Proced. Int., 1995, 27, 129.
5. K. Sonogashira, Y. Tohda and N. Hagihara, Tetrahedron Lett., 1975, 16, 4467; K. Sonogashira, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 3, p. 521; R. Rossi, A. Carpita and F. Bellina, Org. Prep. Proced. Int., 1995, 27, 129.
6. M. Alami, F. Ferri and G. Linstrumella, Tetrahedron Lett., 1993, 34, 6403.
7. For the recent reviews for iodonium salts: P. J. Stang, Angew. Chem., Int. Ed. Engl., 1992, 31, 274; R. M. Moriarty and R. K. Vaid, Synthesis, 1990, 431; M. Ochiai, Rev. Heteroat. Chem., 1989, 2, 92.
8. For the recent reviews for iodonium salts: P. J. Stang, Angew. Chem., Int. Ed. Engl., 1992, 31, 274; R. M. Moriarty and R. K. Vaid, Synthesis, 1990, 431; M. Ochiai, Rev. Heteroat. Chem., 1989, 2, 92.
9. For the recent reviews for iodonium salts: P. J. Stang, Angew. Chem., Int. Ed. Engl., 1992, 31, 274; R. M. Moriarty and R. K. Vaid, Synthesis, 1990, 431; M. Ochiai, Rev. Heteroat. Chem., 1989, 2, 92.
10. S.-K. Kang, K.-Y. Jung, C.-H. Park and S.-B. Jang, Tetrahedron Lett., 1995, 36, 8047.
11. Pd-catalysed C-C bond formation: R. M. Moriarty, W. R. Epa and A. K. Awasthi, J. Am. Chem. Soc., 1991, 113, 6315; R. M. Moriarty and W. R. Epa, Tetrahedron Lett., 1992, 33, 4095; R. J. Hinkle, G. T. Poulter and P. J. Stang, J. Am. Chem. Soc., 1993, 115, 11626; K. Sugioka, M. Uchiyama, T. Suzuki and Y. Yamazaki, Nippon Kagaku Kaishi, 1985, 558; Chem. Abstr., 1986, 104, 109-137.
12. Pd-catalysed C-C bond formation: R. M. Moriarty, W. R. Epa and A. K. Awasthi, J. Am. Chem. Soc., 1991, 113, 6315; R. M. Moriarty and W. R. Epa, Tetrahedron Lett., 1992, 33, 4095; R. J. Hinkle, G. T. Poulter and P. J. Stang, J. Am. Chem. Soc., 1993, 115, 11626; K. Sugioka, M. Uchiyama, T. Suzuki and Y. Yamazaki, Nippon Kagaku Kaishi, 1985, 558; Chem. Abstr., 1986, 104, 109-137.
13. Pd-catalysed C-C bond formation: R. M. Moriarty, W. R. Epa and A. K. Awasthi, J. Am. Chem. Soc., 1991, 113, 6315; R. M. Moriarty and W. R. Epa, Tetrahedron Lett., 1992, 33, 4095; R. J. Hinkle, G. T. Poulter and P. J. Stang, J. Am. Chem. Soc., 1993, 115, 11626; K. Sugioka, M. Uchiyama, T. Suzuki and Y. Yamazaki, Nippon Kagaku Kaishi, 1985, 558; Chem. Abstr., 1986, 104, 109-137.
14. Pd-catalysed C-C bond formation: R. M. Moriarty, W. R. Epa and A. K. Awasthi, J. Am. Chem. Soc., 1991, 113, 6315; R. M. Moriarty and W. R. Epa, Tetrahedron Lett., 1992, 33, 4095; R. J. Hinkle, G. T. Poulter and P. J. Stang, J. Am. Chem. Soc., 1993, 115, 11626; K. Sugioka, M. Uchiyama, T. Suzuki and Y. Yamazaki, Nippon Kagaku Kaishi, 1985, 558; Chem. Abstr., 1986, 104, 109-137.
15. Pd-catalysed C-C bond formation: R. M. Moriarty, W. R. Epa and A. K. Awasthi, J. Am. Chem. Soc., 1991, 113, 6315; R. M. Moriarty and W. R. Epa, Tetrahedron Lett., 1992, 33, 4095; R. J. Hinkle, G. T. Poulter and P. J. Stang, J. Am. Chem. Soc., 1993, 115, 11626; K. Sugioka, M. Uchiyama, T. Suzuki and Y. Yamazaki, Nippon Kagaku Kaishi, 1985, 558; Chem. Abstr., 1986, 104, 109-137.
16. M. Ochiai, K. Sumi, Y. Takaoka, Y. Nagao, M. Shiro and E. Fujita, Tetrahedron, 1988, 44, 4095.
17. A. J. Morgida and G. F. Koser, J. Org. Chem., 1984, 49, 3643.
18. Diacetylene derivatives have been found to display liquid-crystalline and non-linear optical properties. See: A. E. Stiegman, E. Graham, K. J. Perry, L. R. Khundkar, L.-T. Cheng and J. W. Perry, J. Am. Chem. Soc., 1991, 113, 7658; C. Fouquey, J.-M. Lehn and J. Malthete, J. Chem. Soc., Chem. Commun., 1987, 1424.
19. Diacetylene derivatives have been found to display liquid-crystalline and non-linear optical properties. See: A. E. Stiegman, E. Graham, K. J. Perry, L. R. Khundkar, L.-T. Cheng and J. W. Perry, J. Am. Chem. Soc., 1991, 113, 7658; C. Fouquey, J.-M. Lehn and J. Malthete, J. Chem. Soc., Chem. Commun., 1987, 1424.
20. K. Minn, Syntett, 1991, 115.
21. First synthesis: O. Neiland and B. Karek, J. Org. Chem. USSR (Engl. Transl.), 1970, 6, 889; G. F. Koser and R. H. Wettach, J. Org. Chem., 1977, 42, 1476.
22. First synthesis: O. Neiland and B. Karek, J. Org. Chem. USSR (Engl. Transl.), 1970, 6, 889; G. F. Koser and R. H. Wettach, J. Org. Chem., 1977, 42, 1476.
23. N. S. Zefirov, V. V. Zhdankin and A. S. Koz'min, Izv. Akad. Nauk SSR, Ser. Khim., 1983, 1682; V. V. Zefirov, Y. V. Dan'kov and A. S. Koz'min, Zh. Org. Khim., 1984, 20, 446; J. Gallos, A. Varvoglis and N. W. Alcock, J. Chem. Soc., Perkin Trans. I, 1985, 757; R. T. Hembre, C. P. Scott and J. R. Norton, J. Org. Chem., 1987, 52, 3650.
24. N. S. Zefirov, V. V. Zhdankin and A. S. Koz'min, Izv. Akad. Nauk SSR, Ser. Khim., 1983, 1682; V. V. Zefirov, Y. V. Dan'kov and A. S. Koz'min, Zh. Org. Khim., 1984, 20, 446; J. Gallos, A. Varvoglis and N. W. Alcock, J. Chem. Soc., Perkin Trans. I, 1985, 757; R. T. Hembre, C. P. Scott and J. R. Norton, J. Org. Chem., 1987, 52, 3650.
25. N. S. Zefirov, V. V. Zhdankin and A. S. Koz'min, Izv. Akad. Nauk SSR, Ser. Khim., 1983, 1682; V. V. Zefirov, Y. V. Dan'kov and A. S. Koz'min, Zh. Org. Khim., 1984, 20, 446; J. Gallos, A. Varvoglis and N. W. Alcock, J. Chem. Soc., Perkin Trans. I, 1985, 757; R. T. Hembre, C. P. Scott and J. R. Norton, J. Org. Chem., 1987, 52, 3650.
26. N. S. Zefirov, V. V. Zhdankin and A. S. Koz'min, Izv. Akad. Nauk SSR, Ser. Khim., 1983, 1682; V. V. Zefirov, Y. V. Dan'kov and A. S. Koz'min, Zh. Org. Khim., 1984, 20, 446; J. Gallos, A. Varvoglis and N. W. Alcock, J. Chem. Soc., Perkin Trans. I, 1985, 757; R. T. Hembre, C. P. Scott and J. R. Norton, J. Org. Chem., 1987, 52, 3650.