The sonogashira reaction in water via an amphiphilic resin-supported palladium-phosphine complex under copper-free conditions

Heterocycles

Volumn 59, Issue 1, 2003, Pages 71-74

  Uozumi, Yasuhiro ^a   Kobayashi, Yukinari ^a  

^a INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; ALKYNE; BENZOFURAN DERIVATIVE; HALIDE; MACROGOL; POLYSTYRENE; RESIN;

ARTICLE; CATALYSIS; CHEMICAL REACTION; REACTION ANALYSIS;

EID: 0037226411     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-02-S21     Document Type: Article

References (41)

1. K. Sonogashira and Y. Tohda, Tetrahedron Lett., 1975, 4467.
2. For recent examples of palladium-catalyzed heteroannulation forming indoles or benzofurans, see: (a) A. Arcadi and F. Marinelli, Synthesis, 1986, 749. (b) N. G. Kundu, P. Pal, J. S. Mahanti, and S. K. Dasgupta, J. Chem. Soc., Chem. Commun., 1992, 41. (c) R. C. Larock, E. K. Yum, M. J. Doty, and K. K. C. Sham, J. Org. Chem., 1995, 60, 3270. (d) A. Arcadi and F. Marinelli, Tetrahedron Lett., 1992, 33, 3915. (e) T. Sakamoto, Y. Kondo, S. Iwashita, T. Nagano, and H. Yamanaka, Chem. Pharm. Bull. 1988, 36, 1305. (f) R. C. Larock and E. K. Yum, J. Am. Chem. Soc., 1991, 113, 6689. (g) T. Jeschke, D. Wesbo, U. Annby, S. Gronowitz, and L. A. Cohen, Tetrahedron Lett., 1993, 34, 9355. (h) J. Ezquerra, C. Pedregal, J. M. Lamas, J. Barluenga, M. Perez, M. A. Garcia-Martin, and J. M. Gonzalez, J. Org. Chem., 1996, 61, 5804.
3. For recent examples of palladium-catalyzed heteroannulation forming indoles or benzofurans, see: (a) A. Arcadi and F. Marinelli, Synthesis, 1986, 749. (b) N. G. Kundu, P. Pal, J. S. Mahanti, and S. K. Dasgupta, J. Chem. Soc., Chem. Commun., 1992, 41. (c) R. C. Larock, E. K. Yum, M. J. Doty, and K. K. C. Sham, J. Org. Chem., 1995, 60, 3270. (d) A. Arcadi and F. Marinelli, Tetrahedron Lett., 1992, 33, 3915. (e) T. Sakamoto, Y. Kondo, S. Iwashita, T. Nagano, and H. Yamanaka, Chem. Pharm. Bull. 1988, 36, 1305. (f) R. C. Larock and E. K. Yum, J. Am. Chem. Soc., 1991, 113, 6689. (g) T. Jeschke, D. Wesbo, U. Annby, S. Gronowitz, and L. A. Cohen, Tetrahedron Lett., 1993, 34, 9355. (h) J. Ezquerra, C. Pedregal, J. M. Lamas, J. Barluenga, M. Perez, M. A. Garcia-Martin, and J. M. Gonzalez, J. Org. Chem., 1996, 61, 5804.
4. For recent examples of palladium-catalyzed heteroannulation forming indoles or benzofurans, see: (a) A. Arcadi and F. Marinelli, Synthesis, 1986, 749. (b) N. G. Kundu, P. Pal, J. S. Mahanti, and S. K. Dasgupta, J. Chem. Soc., Chem. Commun., 1992, 41. (c) R. C. Larock, E. K. Yum, M. J. Doty, and K. K. C. Sham, J. Org. Chem., 1995, 60, 3270. (d) A. Arcadi and F. Marinelli, Tetrahedron Lett., 1992, 33, 3915. (e) T. Sakamoto, Y. Kondo, S. Iwashita, T. Nagano, and H. Yamanaka, Chem. Pharm. Bull. 1988, 36, 1305. (f) R. C. Larock and E. K. Yum, J. Am. Chem. Soc., 1991, 113, 6689. (g) T. Jeschke, D. Wesbo, U. Annby, S. Gronowitz, and L. A. Cohen, Tetrahedron Lett., 1993, 34, 9355. (h) J. Ezquerra, C. Pedregal, J. M. Lamas, J. Barluenga, M. Perez, M. A. Garcia-Martin, and J. M. Gonzalez, J. Org. Chem., 1996, 61, 5804.
5. For recent examples of palladium-catalyzed heteroannulation forming indoles or benzofurans, see: (a) A. Arcadi and F. Marinelli, Synthesis, 1986, 749. (b) N. G. Kundu, P. Pal, J. S. Mahanti, and S. K. Dasgupta, J. Chem. Soc., Chem. Commun., 1992, 41. (c) R. C. Larock, E. K. Yum, M. J. Doty, and K. K. C. Sham, J. Org. Chem., 1995, 60, 3270. (d) A. Arcadi and F. Marinelli, Tetrahedron Lett., 1992, 33, 3915. (e) T. Sakamoto, Y. Kondo, S. Iwashita, T. Nagano, and H. Yamanaka, Chem. Pharm. Bull. 1988, 36, 1305. (f) R. C. Larock and E. K. Yum, J. Am. Chem. Soc., 1991, 113, 6689. (g) T. Jeschke, D. Wesbo, U. Annby, S. Gronowitz, and L. A. Cohen, Tetrahedron Lett., 1993, 34, 9355. (h) J. Ezquerra, C. Pedregal, J. M. Lamas, J. Barluenga, M. Perez, M. A. Garcia-Martin, and J. M. Gonzalez, J. Org. Chem., 1996, 61, 5804.
6. For recent examples of palladium-catalyzed heteroannulation forming indoles or benzofurans, see: (a) A. Arcadi and F. Marinelli, Synthesis, 1986, 749. (b) N. G. Kundu, P. Pal, J. S. Mahanti, and S. K. Dasgupta, J. Chem. Soc., Chem. Commun., 1992, 41. (c) R. C. Larock, E. K. Yum, M. J. Doty, and K. K. C. Sham, J. Org. Chem., 1995, 60, 3270. (d) A. Arcadi and F. Marinelli, Tetrahedron Lett., 1992, 33, 3915. (e) T. Sakamoto, Y. Kondo, S. Iwashita, T. Nagano, and H. Yamanaka, Chem. Pharm. Bull. 1988, 36, 1305. (f) R. C. Larock and E. K. Yum, J. Am. Chem. Soc., 1991, 113, 6689. (g) T. Jeschke, D. Wesbo, U. Annby, S. Gronowitz, and L. A. Cohen, Tetrahedron Lett., 1993, 34, 9355. (h) J. Ezquerra, C. Pedregal, J. M. Lamas, J. Barluenga, M. Perez, M. A. Garcia-Martin, and J. M. Gonzalez, J. Org. Chem., 1996, 61, 5804.
7. For recent examples of palladium-catalyzed heteroannulation forming indoles or benzofurans, see: (a) A. Arcadi and F. Marinelli, Synthesis, 1986, 749. (b) N. G. Kundu, P. Pal, J. S. Mahanti, and S. K. Dasgupta, J. Chem. Soc., Chem. Commun., 1992, 41. (c) R. C. Larock, E. K. Yum, M. J. Doty, and K. K. C. Sham, J. Org. Chem., 1995, 60, 3270. (d) A. Arcadi and F. Marinelli, Tetrahedron Lett., 1992, 33, 3915. (e) T. Sakamoto, Y. Kondo, S. Iwashita, T. Nagano, and H. Yamanaka, Chem. Pharm. Bull. 1988, 36, 1305. (f) R. C. Larock and E. K. Yum, J. Am. Chem. Soc., 1991, 113, 6689. (g) T. Jeschke, D. Wesbo, U. Annby, S. Gronowitz, and L. A. Cohen, Tetrahedron Lett., 1993, 34, 9355. (h) J. Ezquerra, C. Pedregal, J. M. Lamas, J. Barluenga, M. Perez, M. A. Garcia-Martin, and J. M. Gonzalez, J. Org. Chem., 1996, 61, 5804.
8. For recent examples of palladium-catalyzed heteroannulation forming indoles or benzofurans, see: (a) A. Arcadi and F. Marinelli, Synthesis, 1986, 749. (b) N. G. Kundu, P. Pal, J. S. Mahanti, and S. K. Dasgupta, J. Chem. Soc., Chem. Commun., 1992, 41. (c) R. C. Larock, E. K. Yum, M. J. Doty, and K. K. C. Sham, J. Org. Chem., 1995, 60, 3270. (d) A. Arcadi and F. Marinelli, Tetrahedron Lett., 1992, 33, 3915. (e) T. Sakamoto, Y. Kondo, S. Iwashita, T. Nagano, and H. Yamanaka, Chem. Pharm. Bull. 1988, 36, 1305. (f) R. C. Larock and E. K. Yum, J. Am. Chem. Soc., 1991, 113, 6689. (g) T. Jeschke, D. Wesbo, U. Annby, S. Gronowitz, and L. A. Cohen, Tetrahedron Lett., 1993, 34, 9355. (h) J. Ezquerra, C. Pedregal, J. M. Lamas, J. Barluenga, M. Perez, M. A. Garcia-Martin, and J. M. Gonzalez, J. Org. Chem., 1996, 61, 5804.
9. For recent examples of palladium-catalyzed heteroannulation forming indoles or benzofurans, see: (a) A. Arcadi and F. Marinelli, Synthesis, 1986, 749. (b) N. G. Kundu, P. Pal, J. S. Mahanti, and S. K. Dasgupta, J. Chem. Soc., Chem. Commun., 1992, 41. (c) R. C. Larock, E. K. Yum, M. J. Doty, and K. K. C. Sham, J. Org. Chem., 1995, 60, 3270. (d) A. Arcadi and F. Marinelli, Tetrahedron Lett., 1992, 33, 3915. (e) T. Sakamoto, Y. Kondo, S. Iwashita, T. Nagano, and H. Yamanaka, Chem. Pharm. Bull. 1988, 36, 1305. (f) R. C. Larock and E. K. Yum, J. Am. Chem. Soc., 1991, 113, 6689. (g) T. Jeschke, D. Wesbo, U. Annby, S. Gronowitz, and L. A. Cohen, Tetrahedron Lett., 1993, 34, 9355. (h) J. Ezquerra, C. Pedregal, J. M. Lamas, J. Barluenga, M. Perez, M. A. Garcia-Martin, and J. M. Gonzalez, J. Org. Chem., 1996, 61, 5804.
10. For recent examples of the Sonogashira reaction under copper-free conditions, see: (a) L. Cassar, J. Organomet. Chem., 1975, 93, 253. (b) H. A. Dieck and F. R. Heck, J. Organomet. Chem., 1975, 93, 259. (c) W. B. Austin, N. Bilow, W. J. Kelleghan, and K. S. Y. Lau, J. Org. Chem., 1981, 46, 2280. (d) M. Alami, F. Ferri, and G. Linstrumelle, Tetrahedron Lett., 1993, 34, 6403. (e) J.-F. Nguefack, V. Bolitt, and D. Sinou, Tetrahedron Lett., 1996, 37, 5527. (f) A. Mori, J. Kawashima, T. Shimada, M. Suguro, K. Hirabayashi, and Y. Nishihara, Org. Lett., 2000, 2, 2935. (g) R. W. Wagner, T. E. Johnson, F. Li, and J. S. Lindsey, J. Org. Chem., 1995, 60, 5266. (h) V. P. Bölm and W. A. Herrmann, Eur. J. Org. Chem., 2000, 3679.
11. For recent examples of the Sonogashira reaction under copper-free conditions, see: (a) L. Cassar, J. Organomet. Chem., 1975, 93, 253. (b) H. A. Dieck and F. R. Heck, J. Organomet. Chem., 1975, 93, 259. (c) W. B. Austin, N. Bilow, W. J. Kelleghan, and K. S. Y. Lau, J. Org. Chem., 1981, 46, 2280. (d) M. Alami, F. Ferri, and G. Linstrumelle, Tetrahedron Lett., 1993, 34, 6403. (e) J.-F. Nguefack, V. Bolitt, and D. Sinou, Tetrahedron Lett., 1996, 37, 5527. (f) A. Mori, J. Kawashima, T. Shimada, M. Suguro, K. Hirabayashi, and Y. Nishihara, Org. Lett., 2000, 2, 2935. (g) R. W. Wagner, T. E. Johnson, F. Li, and J. S. Lindsey, J. Org. Chem., 1995, 60, 5266. (h) V. P. Bölm and W. A. Herrmann, Eur. J. Org. Chem., 2000, 3679.
12. For recent examples of the Sonogashira reaction under copper-free conditions, see: (a) L. Cassar, J. Organomet. Chem., 1975, 93, 253. (b) H. A. Dieck and F. R. Heck, J. Organomet. Chem., 1975, 93, 259. (c) W. B. Austin, N. Bilow, W. J. Kelleghan, and K. S. Y. Lau, J. Org. Chem., 1981, 46, 2280. (d) M. Alami, F. Ferri, and G. Linstrumelle, Tetrahedron Lett., 1993, 34, 6403. (e) J.-F. Nguefack, V. Bolitt, and D. Sinou, Tetrahedron Lett., 1996, 37, 5527. (f) A. Mori, J. Kawashima, T. Shimada, M. Suguro, K. Hirabayashi, and Y. Nishihara, Org. Lett., 2000, 2, 2935. (g) R. W. Wagner, T. E. Johnson, F. Li, and J. S. Lindsey, J. Org. Chem., 1995, 60, 5266. (h) V. P. Bölm and W. A. Herrmann, Eur. J. Org. Chem., 2000, 3679.
13. For recent examples of the Sonogashira reaction under copper-free conditions, see: (a) L. Cassar, J. Organomet. Chem., 1975, 93, 253. (b) H. A. Dieck and F. R. Heck, J. Organomet. Chem., 1975, 93, 259. (c) W. B. Austin, N. Bilow, W. J. Kelleghan, and K. S. Y. Lau, J. Org. Chem., 1981, 46, 2280. (d) M. Alami, F. Ferri, and G. Linstrumelle, Tetrahedron Lett., 1993, 34, 6403. (e) J.-F. Nguefack, V. Bolitt, and D. Sinou, Tetrahedron Lett., 1996, 37, 5527. (f) A. Mori, J. Kawashima, T. Shimada, M. Suguro, K. Hirabayashi, and Y. Nishihara, Org. Lett., 2000, 2, 2935. (g) R. W. Wagner, T. E. Johnson, F. Li, and J. S. Lindsey, J. Org. Chem., 1995, 60, 5266. (h) V. P. Bölm and W. A. Herrmann, Eur. J. Org. Chem., 2000, 3679.
14. For recent examples of the Sonogashira reaction under copper-free conditions, see: (a) L. Cassar, J. Organomet. Chem., 1975, 93, 253. (b) H. A. Dieck and F. R. Heck, J. Organomet. Chem., 1975, 93, 259. (c) W. B. Austin, N. Bilow, W. J. Kelleghan, and K. S. Y. Lau, J. Org. Chem., 1981, 46, 2280. (d) M. Alami, F. Ferri, and G. Linstrumelle, Tetrahedron Lett., 1993, 34, 6403. (e) J.-F. Nguefack, V. Bolitt, and D. Sinou, Tetrahedron Lett., 1996, 37, 5527. (f) A. Mori, J. Kawashima, T. Shimada, M. Suguro, K. Hirabayashi, and Y. Nishihara, Org. Lett., 2000, 2, 2935. (g) R. W. Wagner, T. E. Johnson, F. Li, and J. S. Lindsey, J. Org. Chem., 1995, 60, 5266. (h) V. P. Bölm and W. A. Herrmann, Eur. J. Org. Chem., 2000, 3679.
15. For recent examples of the Sonogashira reaction under copper-free conditions, see: (a) L. Cassar, J. Organomet. Chem., 1975, 93, 253. (b) H. A. Dieck and F. R. Heck, J. Organomet. Chem., 1975, 93, 259. (c) W. B. Austin, N. Bilow, W. J. Kelleghan, and K. S. Y. Lau, J. Org. Chem., 1981, 46, 2280. (d) M. Alami, F. Ferri, and G. Linstrumelle, Tetrahedron Lett., 1993, 34, 6403. (e) J.-F. Nguefack, V. Bolitt, and D. Sinou, Tetrahedron Lett., 1996, 37, 5527. (f) A. Mori, J. Kawashima, T. Shimada, M. Suguro, K. Hirabayashi, and Y. Nishihara, Org. Lett., 2000, 2, 2935. (g) R. W. Wagner, T. E. Johnson, F. Li, and J. S. Lindsey, J. Org. Chem., 1995, 60, 5266. (h) V. P. Bölm and W. A. Herrmann, Eur. J. Org. Chem., 2000, 3679.
16. For recent examples of the Sonogashira reaction under copper-free conditions, see: (a) L. Cassar, J. Organomet. Chem., 1975, 93, 253. (b) H. A. Dieck and F. R. Heck, J. Organomet. Chem., 1975, 93, 259. (c) W. B. Austin, N. Bilow, W. J. Kelleghan, and K. S. Y. Lau, J. Org. Chem., 1981, 46, 2280. (d) M. Alami, F. Ferri, and G. Linstrumelle, Tetrahedron Lett., 1993, 34, 6403. (e) J.-F. Nguefack, V. Bolitt, and D. Sinou, Tetrahedron Lett., 1996, 37, 5527. (f) A. Mori, J. Kawashima, T. Shimada, M. Suguro, K. Hirabayashi, and Y. Nishihara, Org. Lett., 2000, 2, 2935. (g) R. W. Wagner, T. E. Johnson, F. Li, and J. S. Lindsey, J. Org. Chem., 1995, 60, 5266. (h) V. P. Bölm and W. A. Herrmann, Eur. J. Org. Chem., 2000, 3679.
17. For recent examples of the Sonogashira reaction under copper-free conditions, see: (a) L. Cassar, J. Organomet. Chem., 1975, 93, 253. (b) H. A. Dieck and F. R. Heck, J. Organomet. Chem., 1975, 93, 259. (c) W. B. Austin, N. Bilow, W. J. Kelleghan, and K. S. Y. Lau, J. Org. Chem., 1981, 46, 2280. (d) M. Alami, F. Ferri, and G. Linstrumelle, Tetrahedron Lett., 1993, 34, 6403. (e) J.-F. Nguefack, V. Bolitt, and D. Sinou, Tetrahedron Lett., 1996, 37, 5527. (f) A. Mori, J. Kawashima, T. Shimada, M. Suguro, K. Hirabayashi, and Y. Nishihara, Org. Lett., 2000, 2, 2935. (g) R. W. Wagner, T. E. Johnson, F. Li, and J. S. Lindsey, J. Org. Chem., 1995, 60, 5266. (h) V. P. Bölm and W. A. Herrmann, Eur. J. Org. Chem., 2000, 3679.
18. For a recent review of solid-phase reactions using palladium catalysts, see: Y. Uozumi and T. Hayashi, "Solid-Phase Palladium Catalysis for High-throughput Organic Synthesis" in Handbook of Combinatorial Chemistry (Ch. 19), ed. by K. C. Nicolaou, R. Hanko, and W. Hartwig, Wiley-VCH, Weinheim, 2002.
19. For examples of the solid-phase Sonogashira reaction, see: (a) S. Berteina, S. Wendeborn, W. K. -D. Brill, and A. D. Mesmaeker, Synlett 1998, 676. (b) S. I. Kahn and M. W. Grinstaff, J. Am. Chem. Soc., 1999, 121, 4704. (c) S. Huang and J. M. Tour, J. Am. Chem. Soc., 1999, 121, 4908.
20. For examples of the solid-phase Sonogashira reaction, see: (a) S. Berteina, S. Wendeborn, W. K. -D. Brill, and A. D. Mesmaeker, Synlett 1998, 676. (b) S. I. Kahn and M. W. Grinstaff, J. Am. Chem. Soc., 1999, 121, 4704. (c) S. Huang and J. M. Tour, J. Am. Chem. Soc., 1999, 121, 4908.
21. For examples of the solid-phase Sonogashira reaction, see: (a) S. Berteina, S. Wendeborn, W. K. -D. Brill, and A. D. Mesmaeker, Synlett 1998, 676. (b) S. I. Kahn and M. W. Grinstaff, J. Am. Chem. Soc., 1999, 121, 4704. (c) S. Huang and J. M. Tour, J. Am. Chem. Soc., 1999, 121, 4908.
22. For examples of solid-phase heteroannulation via the Sonogashira reaction, see: (a) M. C. Fagnola, I. Candiani, G. Visentin, W. Cabri, F. Zarini, N. Mongelli, and A. Bedeschi, Tetrahedron Lett., 1997, 38, 2307. (b) H-C. Zhang, K. K. Brumfield, L. Jaroskova, and B. E. Maryanoff, Tetrahedron Lett., 1998, 39, 4449. (c) D. Fancelli, M. C. Fagnola, D. Severino, and A. Bedeschi, Tetrahedron Lett., 1997, 38, 2311. (d) M. D. Collini and J. W. Ellingboe, Tetrahedron Lett., 1997, 38, 7963.
23. For examples of solid-phase heteroannulation via the Sonogashira reaction, see: (a) M. C. Fagnola, I. Candiani, G. Visentin, W. Cabri, F. Zarini, N. Mongelli, and A. Bedeschi, Tetrahedron Lett., 1997, 38, 2307. (b) H-C. Zhang, K. K. Brumfield, L. Jaroskova, and B. E. Maryanoff, Tetrahedron Lett., 1998, 39, 4449. (c) D. Fancelli, M. C. Fagnola, D. Severino, and A. Bedeschi, Tetrahedron Lett., 1997, 38, 2311. (d) M. D. Collini and J. W. Ellingboe, Tetrahedron Lett., 1997, 38, 7963.
24. For examples of solid-phase heteroannulation via the Sonogashira reaction, see: (a) M. C. Fagnola, I. Candiani, G. Visentin, W. Cabri, F. Zarini, N. Mongelli, and A. Bedeschi, Tetrahedron Lett., 1997, 38, 2307. (b) H-C. Zhang, K. K. Brumfield, L. Jaroskova, and B. E. Maryanoff, Tetrahedron Lett., 1998, 39, 4449. (c) D. Fancelli, M. C. Fagnola, D. Severino, and A. Bedeschi, Tetrahedron Lett., 1997, 38, 2311. (d) M. D. Collini and J. W. Ellingboe, Tetrahedron Lett., 1997, 38, 7963.
25. For examples of solid-phase heteroannulation via the Sonogashira reaction, see: (a) M. C. Fagnola, I. Candiani, G. Visentin, W. Cabri, F. Zarini, N. Mongelli, and A. Bedeschi, Tetrahedron Lett., 1997, 38, 2307. (b) H-C. Zhang, K. K. Brumfield, L. Jaroskova, and B. E. Maryanoff, Tetrahedron Lett., 1998, 39, 4449. (c) D. Fancelli, M. C. Fagnola, D. Severino, and A. Bedeschi, Tetrahedron Lett., 1997, 38, 2311. (d) M. D. Collini and J. W. Ellingboe, Tetrahedron Lett., 1997, 38, 7963.
26. (a) Y. Uozumi, H. Danjo, and T. Hayashi, Tetrahedron Lett., 1997, 38, 3557.
27. (b) H. Danjo, D. Tanaka, T. Hayashi, and Y. Uozumi, Tetrahedron, 1999, 55, 14341.
28. (c) Y. Uozumi and T. Watanabe, J. Org. Chem., 1999, 64, 6921.
29. (d) Y. Uozumi, H. Danjo, and T. Hayashi, J. Org. Chem., 1999, 64, 3384.
30. The Sonogashira reaction was performed in an aqueous organic solvent. For a review, see: (a) J. P. Genet and M. Savignac, J. Organomet. Chem., 1999, 576, 305. For recent examples, see: (b) A. L. Casalnuovo and J. C. Calabrese, J. Am. Chem. Soc., 1990, 112, 4324. (c) J. P. Genet, E. Blart, and M. Savignac, Synlett, 1992, 715. (d) C. Amatore, E. Blart, J. P. Genet, A. Jutand, S. Lemaire-Audoire, and M. Savignac, J. Org. Chem., 1995, 60, 6829. (e) N. A. Bumagin, L. I. Sukhomlinova, E. V. Luzikova, T. P. Tolstaya, and I. Beletskaya, Tetrahedron Lett., 1996, 37, 897. (f) D. E. Bergbreiter and Y.-S. Liu, Tetrahedron Lett., 1997, 38, 7843. (g) H. Dibowski and F. P. Schmidtchen, Tetrahedron Lett., 1998, 39, 525. (h) D. T. Bong and M. R. Ghadiri, Org. Lett., 2001, 3, 2509. (i) M. P. López-Deber, L. Castedo, and J. R. Granja, Org. Lett., 2001, 2, 2823. See also ref. 3e.
31. The Sonogashira reaction was performed in an aqueous organic solvent. For a review, see: (a) J. P. Genet and M. Savignac, J. Organomet. Chem., 1999, 576, 305. For recent examples, see: (b) A. L. Casalnuovo and J. C. Calabrese, J. Am. Chem. Soc., 1990, 112, 4324. (c) J. P. Genet, E. Blart, and M. Savignac, Synlett, 1992, 715. (d) C. Amatore, E. Blart, J. P. Genet, A. Jutand, S. Lemaire-Audoire, and M. Savignac, J. Org. Chem., 1995, 60, 6829. (e) N. A. Bumagin, L. I. Sukhomlinova, E. V. Luzikova, T. P. Tolstaya, and I. Beletskaya, Tetrahedron Lett., 1996, 37, 897. (f) D. E. Bergbreiter and Y.-S. Liu, Tetrahedron Lett., 1997, 38, 7843. (g) H. Dibowski and F. P. Schmidtchen, Tetrahedron Lett., 1998, 39, 525. (h) D. T. Bong and M. R. Ghadiri, Org. Lett., 2001, 3, 2509. (i) M. P. López-Deber, L. Castedo, and J. R. Granja, Org. Lett., 2001, 2, 2823. See also ref. 3e.
32. The Sonogashira reaction was performed in an aqueous organic solvent. For a review, see: (a) J. P. Genet and M. Savignac, J. Organomet. Chem., 1999, 576, 305. For recent examples, see: (b) A. L. Casalnuovo and J. C. Calabrese, J. Am. Chem. Soc., 1990, 112, 4324. (c) J. P. Genet, E. Blart, and M. Savignac, Synlett, 1992, 715. (d) C. Amatore, E. Blart, J. P. Genet, A. Jutand, S. Lemaire-Audoire, and M. Savignac, J. Org. Chem., 1995, 60, 6829. (e) N. A. Bumagin, L. I. Sukhomlinova, E. V. Luzikova, T. P. Tolstaya, and I. Beletskaya, Tetrahedron Lett., 1996, 37, 897. (f) D. E. Bergbreiter and Y.-S. Liu, Tetrahedron Lett., 1997, 38, 7843. (g) H. Dibowski and F. P. Schmidtchen, Tetrahedron Lett., 1998, 39, 525. (h) D. T. Bong and M. R. Ghadiri, Org. Lett., 2001, 3, 2509. (i) M. P. López-Deber, L. Castedo, and J. R. Granja, Org. Lett., 2001, 2, 2823. See also ref. 3e.
33. The Sonogashira reaction was performed in an aqueous organic solvent. For a review, see: (a) J. P. Genet and M. Savignac, J. Organomet. Chem., 1999, 576, 305. For recent examples, see: (b) A. L. Casalnuovo and J. C. Calabrese, J. Am. Chem. Soc., 1990, 112, 4324. (c) J. P. Genet, E. Blart, and M. Savignac, Synlett, 1992, 715. (d) C. Amatore, E. Blart, J. P. Genet, A. Jutand, S. Lemaire-Audoire, and M. Savignac, J. Org. Chem., 1995, 60, 6829. (e) N. A. Bumagin, L. I. Sukhomlinova, E. V. Luzikova, T. P. Tolstaya, and I. Beletskaya, Tetrahedron Lett., 1996, 37, 897. (f) D. E. Bergbreiter and Y.-S. Liu, Tetrahedron Lett., 1997, 38, 7843. (g) H. Dibowski and F. P. Schmidtchen, Tetrahedron Lett., 1998, 39, 525. (h) D. T. Bong and M. R. Ghadiri, Org. Lett., 2001, 3, 2509. (i) M. P. López-Deber, L. Castedo, and J. R. Granja, Org. Lett., 2001, 2, 2823. See also ref. 3e.
34. The Sonogashira reaction was performed in an aqueous organic solvent. For a review, see: (a) J. P. Genet and M. Savignac, J. Organomet. Chem., 1999, 576, 305. For recent examples, see: (b) A. L. Casalnuovo and J. C. Calabrese, J. Am. Chem. Soc., 1990, 112, 4324. (c) J. P. Genet, E. Blart, and M. Savignac, Synlett, 1992, 715. (d) C. Amatore, E. Blart, J. P. Genet, A. Jutand, S. Lemaire-Audoire, and M. Savignac, J. Org. Chem., 1995, 60, 6829. (e) N. A. Bumagin, L. I. Sukhomlinova, E. V. Luzikova, T. P. Tolstaya, and I. Beletskaya, Tetrahedron Lett., 1996, 37, 897. (f) D. E. Bergbreiter and Y.-S. Liu, Tetrahedron Lett., 1997, 38, 7843. (g) H. Dibowski and F. P. Schmidtchen, Tetrahedron Lett., 1998, 39, 525. (h) D. T. Bong and M. R. Ghadiri, Org. Lett., 2001, 3, 2509. (i) M. P. López-Deber, L. Castedo, and J. R. Granja, Org. Lett., 2001, 2, 2823. See also ref. 3e.
35. The Sonogashira reaction was performed in an aqueous organic solvent. For a review, see: (a) J. P. Genet and M. Savignac, J. Organomet. Chem., 1999, 576, 305. For recent examples, see: (b) A. L. Casalnuovo and J. C. Calabrese, J. Am. Chem. Soc., 1990, 112, 4324. (c) J. P. Genet, E. Blart, and M. Savignac, Synlett, 1992, 715. (d) C. Amatore, E. Blart, J. P. Genet, A. Jutand, S. Lemaire-Audoire, and M. Savignac, J. Org. Chem., 1995, 60, 6829. (e) N. A. Bumagin, L. I. Sukhomlinova, E. V. Luzikova, T. P. Tolstaya, and I. Beletskaya, Tetrahedron Lett., 1996, 37, 897. (f) D. E. Bergbreiter and Y.-S. Liu, Tetrahedron Lett., 1997, 38, 7843. (g) H. Dibowski and F. P. Schmidtchen, Tetrahedron Lett., 1998, 39, 525. (h) D. T. Bong and M. R. Ghadiri, Org. Lett., 2001, 3, 2509. (i) M. P. López-Deber, L. Castedo, and J. R. Granja, Org. Lett., 2001, 2, 2823. See also ref. 3e.
36. The Sonogashira reaction was performed in an aqueous organic solvent. For a review, see: (a) J. P. Genet and M. Savignac, J. Organomet. Chem., 1999, 576, 305. For recent examples, see: (b) A. L. Casalnuovo and J. C. Calabrese, J. Am. Chem. Soc., 1990, 112, 4324. (c) J. P. Genet, E. Blart, and M. Savignac, Synlett, 1992, 715. (d) C. Amatore, E. Blart, J. P. Genet, A. Jutand, S. Lemaire-Audoire, and M. Savignac, J. Org. Chem., 1995, 60, 6829. (e) N. A. Bumagin, L. I. Sukhomlinova, E. V. Luzikova, T. P. Tolstaya, and I. Beletskaya, Tetrahedron Lett., 1996, 37, 897. (f) D. E. Bergbreiter and Y.-S. Liu, Tetrahedron Lett., 1997, 38, 7843. (g) H. Dibowski and F. P. Schmidtchen, Tetrahedron Lett., 1998, 39, 525. (h) D. T. Bong and M. R. Ghadiri, Org. Lett., 2001, 3, 2509. (i) M. P. López-Deber, L. Castedo, and J. R. Granja, Org. Lett., 2001, 2, 2823. See also ref. 3e.
37. The Sonogashira reaction was performed in an aqueous organic solvent. For a review, see: (a) J. P. Genet and M. Savignac, J. Organomet. Chem., 1999, 576, 305. For recent examples, see: (b) A. L. Casalnuovo and J. C. Calabrese, J. Am. Chem. Soc., 1990, 112, 4324. (c) J. P. Genet, E. Blart, and M. Savignac, Synlett, 1992, 715. (d) C. Amatore, E. Blart, J. P. Genet, A. Jutand, S. Lemaire-Audoire, and M. Savignac, J. Org. Chem., 1995, 60, 6829. (e) N. A. Bumagin, L. I. Sukhomlinova, E. V. Luzikova, T. P. Tolstaya, and I. Beletskaya, Tetrahedron Lett., 1996, 37, 897. (f) D. E. Bergbreiter and Y.-S. Liu, Tetrahedron Lett., 1997, 38, 7843. (g) H. Dibowski and F. P. Schmidtchen, Tetrahedron Lett., 1998, 39, 525. (h) D. T. Bong and M. R. Ghadiri, Org. Lett., 2001, 3, 2509. (i) M. P. López-Deber, L. Castedo, and J. R. Granja, Org. Lett., 2001, 2, 2823. See also ref. 3e.
38. The Sonogashira reaction was performed in an aqueous organic solvent. For a review, see: (a) J. P. Genet and M. Savignac, J. Organomet. Chem., 1999, 576, 305. For recent examples, see: (b) A. L. Casalnuovo and J. C. Calabrese, J. Am. Chem. Soc., 1990, 112, 4324. (c) J. P. Genet, E. Blart, and M. Savignac, Synlett, 1992, 715. (d) C. Amatore, E. Blart, J. P. Genet, A. Jutand, S. Lemaire-Audoire, and M. Savignac, J. Org. Chem., 1995, 60, 6829. (e) N. A. Bumagin, L. I. Sukhomlinova, E. V. Luzikova, T. P. Tolstaya, and I. Beletskaya, Tetrahedron Lett., 1996, 37, 897. (f) D. E. Bergbreiter and Y.-S. Liu, Tetrahedron Lett., 1997, 38, 7843. (g) H. Dibowski and F. P. Schmidtchen, Tetrahedron Lett., 1998, 39, 525. (h) D. T. Bong and M. R. Ghadiri, Org. Lett., 2001, 3, 2509. (i) M. P. López-Deber, L. Castedo, and J. R. Granja, Org. Lett., 2001, 2, 2823. See also ref. 3e.
39. A copper-free Sonogashira reaction in ionic liquids has recently been reported, see: T. Fukuyama, M. Shinmen, S. Nishitani, M. Sato, and I. Ryu, Org. Lett., 2002, 4, 1691.
40. Recently, it has been reported that cesium bases efficiently promoted a 5-endo-dig cyclization of 2-alkynyl-anilines forming the indole framework, see: A. L. Rodriguez, C. Koradin, W. Dohle, and P. Knochel, Angew. Chemie. Int. Ed. Engl. 2000, 39, 2488.
41. Chemical Abstract Registry numbers for 7a-e have been provided by the author: 7a, [1839-72-1]; 7b, [19234-04-9]; 7c, [25664-48-6]; 7d, [69976-38-1]; 7e, [46967-97-9].