Palladium- and copper-catalyzed homocoupling of organolead compounds: Synthesis of biaryls and diynes

Synthetic Communications

Volumn 27, Issue 11, 1997, Pages 1893-1897

  Kang, Suk Ku ^a   Shivkumar, Uma ^a   Ahn, Chuljin ^a   Choi, Sang Chul ^a   Kim, Jae Sun ^a  

^a Sungkyunkwan University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; COPPER; HALIDE; ORGANOLEAD COMPOUND; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DIMERIZATION; ORGANIC CHEMISTRY; REACTION ANALYSIS; SYNTHESIS;

EID: 0030906733     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919708006790     Document Type: Article

References (19)

1. Anton, U.; Goeltner, C.; Muellen, K. Chem. Ber. 1992, 125, 2325-2330.
2. (a) Gray, G. W. "Molecular Structures and the Properties of Liquid Crystals." Academic Press : London, 1962.
3. (b) Solladie, G.; Gottarelli, G. Tetrahedron 1987, 43, 1425-1437.
4. Ni-Catalyzed homocoupling: (a) Semmelhack, M. F.; Helquist, P. M.; Jones, L. D. J. Am. Chem. Soc. 1971, 93, 5908-5910. (b) Yamashita, J.; Inoue, Y.; Kondo, T.; Hashimoto, H. Chem. Lett. 1986, 407-408. (c) Colon, I.; Kelsey, D. R. J. Org. Chem, 1986, 51, 2627-2637. (d) Laurak, M.; Vanderesse, R.; Fort, Y.; Caubere, P. J. Org. Chem. 1989, 54, 4840-4844. (e) Iyoda, M.; Otsuka, H.; Sato, K.; Nisato, N.; Oda, M. Bull. Chem. Soc. Jpn. 1990, 63, 80-87. (f) Jutand, A.; Mosleh, A. Synlett 1993, 568-570. Palladium-catalyzed homocoupling: (g) Clark, F. R. S.; Norman, R. O. C.; Thomas, C. B. J. Chem. Soc. Perkin Trans. I 1975, 121-125. (h) Bamfield, P.; Quan, P. M. Synthesis 1978, 537-538. (i) Barton, D. H. R.; Ozbalik, N.; Ramesh, M. Tetrahedron 1988, 44, 5661-5668. (j) Miura, M.; Hashimoto, H.; Itoh, K.; Nomura, M. Chem. Lett. 1990, 459-460. Others : (k) Kretchmer, R. A.; Glowinski, R. J. Org. Chem. 1976, 41, 2661-2662.
5. Ni-Catalyzed homocoupling: (a) Semmelhack, M. F.; Helquist, P. M.; Jones, L. D. J. Am. Chem. Soc. 1971, 93, 5908-5910. (b) Yamashita, J.; Inoue, Y.; Kondo, T.; Hashimoto, H. Chem. Lett. 1986, 407-408. (c) Colon, I.; Kelsey, D. R. J. Org. Chem, 1986, 51, 2627-2637. (d) Laurak, M.; Vanderesse, R.; Fort, Y.; Caubere, P. J. Org. Chem. 1989, 54, 4840-4844. (e) Iyoda, M.; Otsuka, H.; Sato, K.; Nisato, N.; Oda, M. Bull. Chem. Soc. Jpn. 1990, 63, 80-87. (f) Jutand, A.; Mosleh, A. Synlett 1993, 568-570. Palladium-catalyzed homocoupling: (g) Clark, F. R. S.; Norman, R. O. C.; Thomas, C. B. J. Chem. Soc. Perkin Trans. I 1975, 121-125. (h) Bamfield, P.; Quan, P. M. Synthesis 1978, 537-538. (i) Barton, D. H. R.; Ozbalik, N.; Ramesh, M. Tetrahedron 1988, 44, 5661-5668. (j) Miura, M.; Hashimoto, H.; Itoh, K.; Nomura, M. Chem. Lett. 1990, 459-460. Others : (k) Kretchmer, R. A.; Glowinski, R. J. Org. Chem. 1976, 41, 2661-2662.
6. Ni-Catalyzed homocoupling: (a) Semmelhack, M. F.; Helquist, P. M.; Jones, L. D. J. Am. Chem. Soc. 1971, 93, 5908-5910. (b) Yamashita, J.; Inoue, Y.; Kondo, T.; Hashimoto, H. Chem. Lett. 1986, 407-408. (c) Colon, I.; Kelsey, D. R. J. Org. Chem, 1986, 51, 2627-2637. (d) Laurak, M.; Vanderesse, R.; Fort, Y.; Caubere, P. J. Org. Chem. 1989, 54, 4840-4844. (e) Iyoda, M.; Otsuka, H.; Sato, K.; Nisato, N.; Oda, M. Bull. Chem. Soc. Jpn. 1990, 63, 80-87. (f) Jutand, A.; Mosleh, A. Synlett 1993, 568-570. Palladium-catalyzed homocoupling: (g) Clark, F. R. S.; Norman, R. O. C.; Thomas, C. B. J. Chem. Soc. Perkin Trans. I 1975, 121-125. (h) Bamfield, P.; Quan, P. M. Synthesis 1978, 537-538. (i) Barton, D. H. R.; Ozbalik, N.; Ramesh, M. Tetrahedron 1988, 44, 5661-5668. (j) Miura, M.; Hashimoto, H.; Itoh, K.; Nomura, M. Chem. Lett. 1990, 459-460. Others : (k) Kretchmer, R. A.; Glowinski, R. J. Org. Chem. 1976, 41, 2661-2662.
7. Ni-Catalyzed homocoupling: (a) Semmelhack, M. F.; Helquist, P. M.; Jones, L. D. J. Am. Chem. Soc. 1971, 93, 5908-5910. (b) Yamashita, J.; Inoue, Y.; Kondo, T.; Hashimoto, H. Chem. Lett. 1986, 407-408. (c) Colon, I.; Kelsey, D. R. J. Org. Chem, 1986, 51, 2627-2637. (d) Laurak, M.; Vanderesse, R.; Fort, Y.; Caubere, P. J. Org. Chem. 1989, 54, 4840-4844. (e) Iyoda, M.; Otsuka, H.; Sato, K.; Nisato, N.; Oda, M. Bull. Chem. Soc. Jpn. 1990, 63, 80-87. (f) Jutand, A.; Mosleh, A. Synlett 1993, 568-570. Palladium-catalyzed homocoupling: (g) Clark, F. R. S.; Norman, R. O. C.; Thomas, C. B. J. Chem. Soc. Perkin Trans. I 1975, 121-125. (h) Bamfield, P.; Quan, P. M. Synthesis 1978, 537-538. (i) Barton, D. H. R.; Ozbalik, N.; Ramesh, M. Tetrahedron 1988, 44, 5661-5668. (j) Miura, M.; Hashimoto, H.; Itoh, K.; Nomura, M. Chem. Lett. 1990, 459-460. Others : (k) Kretchmer, R. A.; Glowinski, R. J. Org. Chem. 1976, 41, 2661-2662.
8. Ni-Catalyzed homocoupling: (a) Semmelhack, M. F.; Helquist, P. M.; Jones, L. D. J. Am. Chem. Soc. 1971, 93, 5908-5910. (b) Yamashita, J.; Inoue, Y.; Kondo, T.; Hashimoto, H. Chem. Lett. 1986, 407-408. (c) Colon, I.; Kelsey, D. R. J. Org. Chem, 1986, 51, 2627-2637. (d) Laurak, M.; Vanderesse, R.; Fort, Y.; Caubere, P. J. Org. Chem. 1989, 54, 4840-4844. (e) Iyoda, M.; Otsuka, H.; Sato, K.; Nisato, N.; Oda, M. Bull. Chem. Soc. Jpn. 1990, 63, 80-87. (f) Jutand, A.; Mosleh, A. Synlett 1993, 568-570. Palladium-catalyzed homocoupling: (g) Clark, F. R. S.; Norman, R. O. C.; Thomas, C. B. J. Chem. Soc. Perkin Trans. I 1975, 121-125. (h) Bamfield, P.; Quan, P. M. Synthesis 1978, 537-538. (i) Barton, D. H. R.; Ozbalik, N.; Ramesh, M. Tetrahedron 1988, 44, 5661-5668. (j) Miura, M.; Hashimoto, H.; Itoh, K.; Nomura, M. Chem. Lett. 1990, 459-460. Others : (k) Kretchmer, R. A.; Glowinski, R. J. Org. Chem. 1976, 41, 2661-2662.
9. Ni-Catalyzed homocoupling: (a) Semmelhack, M. F.; Helquist, P. M.; Jones, L. D. J. Am. Chem. Soc. 1971, 93, 5908-5910. (b) Yamashita, J.; Inoue, Y.; Kondo, T.; Hashimoto, H. Chem. Lett. 1986, 407-408. (c) Colon, I.; Kelsey, D. R. J. Org. Chem, 1986, 51, 2627-2637. (d) Laurak, M.; Vanderesse, R.; Fort, Y.; Caubere, P. J. Org. Chem. 1989, 54, 4840-4844. (e) Iyoda, M.; Otsuka, H.; Sato, K.; Nisato, N.; Oda, M. Bull. Chem. Soc. Jpn. 1990, 63, 80-87. (f) Jutand, A.; Mosleh, A. Synlett 1993, 568-570. Palladium-catalyzed homocoupling: (g) Clark, F. R. S.; Norman, R. O. C.; Thomas, C. B. J. Chem. Soc. Perkin Trans. I 1975, 121-125. (h) Bamfield, P.; Quan, P. M. Synthesis 1978, 537-538. (i) Barton, D. H. R.; Ozbalik, N.; Ramesh, M. Tetrahedron 1988, 44, 5661-5668. (j) Miura, M.; Hashimoto, H.; Itoh, K.; Nomura, M. Chem. Lett. 1990, 459-460. Others : (k) Kretchmer, R. A.; Glowinski, R. J. Org. Chem. 1976, 41, 2661-2662.
10. Ni-Catalyzed homocoupling: (a) Semmelhack, M. F.; Helquist, P. M.; Jones, L. D. J. Am. Chem. Soc. 1971, 93, 5908-5910. (b) Yamashita, J.; Inoue, Y.; Kondo, T.; Hashimoto, H. Chem. Lett. 1986, 407-408. (c) Colon, I.; Kelsey, D. R. J. Org. Chem, 1986, 51, 2627-2637. (d) Laurak, M.; Vanderesse, R.; Fort, Y.; Caubere, P. J. Org. Chem. 1989, 54, 4840-4844. (e) Iyoda, M.; Otsuka, H.; Sato, K.; Nisato, N.; Oda, M. Bull. Chem. Soc. Jpn. 1990, 63, 80-87. (f) Jutand, A.; Mosleh, A. Synlett 1993, 568-570. Palladium-catalyzed homocoupling: (g) Clark, F. R. S.; Norman, R. O. C.; Thomas, C. B. J. Chem. Soc. Perkin Trans. I 1975, 121-125. (h) Bamfield, P.; Quan, P. M. Synthesis 1978, 537-538. (i) Barton, D. H. R.; Ozbalik, N.; Ramesh, M. Tetrahedron 1988, 44, 5661-5668. (j) Miura, M.; Hashimoto, H.; Itoh, K.; Nomura, M. Chem. Lett. 1990, 459-460. Others : (k) Kretchmer, R. A.; Glowinski, R. J. Org. Chem. 1976, 41, 2661-2662.
11. Ni-Catalyzed homocoupling: (a) Semmelhack, M. F.; Helquist, P. M.; Jones, L. D. J. Am. Chem. Soc. 1971, 93, 5908-5910. (b) Yamashita, J.; Inoue, Y.; Kondo, T.; Hashimoto, H. Chem. Lett. 1986, 407-408. (c) Colon, I.; Kelsey, D. R. J. Org. Chem, 1986, 51, 2627-2637. (d) Laurak, M.; Vanderesse, R.; Fort, Y.; Caubere, P. J. Org. Chem. 1989, 54, 4840-4844. (e) Iyoda, M.; Otsuka, H.; Sato, K.; Nisato, N.; Oda, M. Bull. Chem. Soc. Jpn. 1990, 63, 80-87. (f) Jutand, A.; Mosleh, A. Synlett 1993, 568-570. Palladium-catalyzed homocoupling: (g) Clark, F. R. S.; Norman, R. O. C.; Thomas, C. B. J. Chem. Soc. Perkin Trans. I 1975, 121-125. (h) Bamfield, P.; Quan, P. M. Synthesis 1978, 537-538. (i) Barton, D. H. R.; Ozbalik, N.; Ramesh, M. Tetrahedron 1988, 44, 5661-5668. (j) Miura, M.; Hashimoto, H.; Itoh, K.; Nomura, M. Chem. Lett. 1990, 459-460. Others : (k) Kretchmer, R. A.; Glowinski, R. J. Org. Chem. 1976, 41, 2661-2662.
12. Ni-Catalyzed homocoupling: (a) Semmelhack, M. F.; Helquist, P. M.; Jones, L. D. J. Am. Chem. Soc. 1971, 93, 5908-5910. (b) Yamashita, J.; Inoue, Y.; Kondo, T.; Hashimoto, H. Chem. Lett. 1986, 407-408. (c) Colon, I.; Kelsey, D. R. J. Org. Chem, 1986, 51, 2627-2637. (d) Laurak, M.; Vanderesse, R.; Fort, Y.; Caubere, P. J. Org. Chem. 1989, 54, 4840-4844. (e) Iyoda, M.; Otsuka, H.; Sato, K.; Nisato, N.; Oda, M. Bull. Chem. Soc. Jpn. 1990, 63, 80-87. (f) Jutand, A.; Mosleh, A. Synlett 1993, 568-570. Palladium-catalyzed homocoupling: (g) Clark, F. R. S.; Norman, R. O. C.; Thomas, C. B. J. Chem. Soc. Perkin Trans. I 1975, 121-125. (h) Bamfield, P.; Quan, P. M. Synthesis 1978, 537-538. (i) Barton, D. H. R.; Ozbalik, N.; Ramesh, M. Tetrahedron 1988, 44, 5661-5668. (j) Miura, M.; Hashimoto, H.; Itoh, K.; Nomura, M. Chem. Lett. 1990, 459-460. Others : (k) Kretchmer, R. A.; Glowinski, R. J. Org. Chem. 1976, 41, 2661-2662.
13. Ni-Catalyzed homocoupling: (a) Semmelhack, M. F.; Helquist, P. M.; Jones, L. D. J. Am. Chem. Soc. 1971, 93, 5908-5910. (b) Yamashita, J.; Inoue, Y.; Kondo, T.; Hashimoto, H. Chem. Lett. 1986, 407-408. (c) Colon, I.; Kelsey, D. R. J. Org. Chem, 1986, 51, 2627-2637. (d) Laurak, M.; Vanderesse, R.; Fort, Y.; Caubere, P. J. Org. Chem. 1989, 54, 4840-4844. (e) Iyoda, M.; Otsuka, H.; Sato, K.; Nisato, N.; Oda, M. Bull. Chem. Soc. Jpn. 1990, 63, 80-87. (f) Jutand, A.; Mosleh, A. Synlett 1993, 568-570. Palladium-catalyzed homocoupling: (g) Clark, F. R. S.; Norman, R. O. C.; Thomas, C. B. J. Chem. Soc. Perkin Trans. I 1975, 121-125. (h) Bamfield, P.; Quan, P. M. Synthesis 1978, 537-538. (i) Barton, D. H. R.; Ozbalik, N.; Ramesh, M. Tetrahedron 1988, 44, 5661-5668. (j) Miura, M.; Hashimoto, H.; Itoh, K.; Nomura, M. Chem. Lett. 1990, 459-460. Others : (k) Kretchmer, R. A.; Glowinski, R. J. Org. Chem. 1976, 41, 2661-2662.
14. Ni-Catalyzed homocoupling: (a) Semmelhack, M. F.; Helquist, P. M.; Jones, L. D. J. Am. Chem. Soc. 1971, 93, 5908-5910. (b) Yamashita, J.; Inoue, Y.; Kondo, T.; Hashimoto, H. Chem. Lett. 1986, 407-408. (c) Colon, I.; Kelsey, D. R. J. Org. Chem, 1986, 51, 2627-2637. (d) Laurak, M.; Vanderesse, R.; Fort, Y.; Caubere, P. J. Org. Chem. 1989, 54, 4840-4844. (e) Iyoda, M.; Otsuka, H.; Sato, K.; Nisato, N.; Oda, M. Bull. Chem. Soc. Jpn. 1990, 63, 80-87. (f) Jutand, A.; Mosleh, A. Synlett 1993, 568-570. Palladium-catalyzed homocoupling: (g) Clark, F. R. S.; Norman, R. O. C.; Thomas, C. B. J. Chem. Soc. Perkin Trans. I 1975, 121-125. (h) Bamfield, P.; Quan, P. M. Synthesis 1978, 537-538. (i) Barton, D. H. R.; Ozbalik, N.; Ramesh, M. Tetrahedron 1988, 44, 5661-5668. (j) Miura, M.; Hashimoto, H.; Itoh, K.; Nomura, M. Chem. Lett. 1990, 459-460. Others : (k) Kretchmer, R. A.; Glowinski, R. J. Org. Chem. 1976, 41, 2661-2662.
15. (a) Torii, S.; Tanaka, H.; Mirisaki, K. Tetrahedron Lett. 1985, 26, 1655-1658.
16. (b) Jutand, A.; Negri, S.; Mosleh, A. J. Chem. Soc. Chem. Commun. 1992, 1729-1730.
17. Review for organolead compounds: Pinhey, J. T. Pure & Appl. Chem. 1996, 68, 819-824.
18. Diacetylenes have been found to display liquid-crystalline and non-linear optical properties: Stiegman, A. E.; Graham, E.; Perry, K-J.; Khumdkar, L. R.; Cheng, L.-T.; Perry, J. W. J. Am. Chem. Soc. 1991, 113, 7658-7666.
19. Diacetylenes can be synthesized by oxidative dimerization of acetylenes: Valenti, E.; Pericas, M. A.; Serratosa, F. J. Am. Chem. Soc. 1990, 112, 7405-7406.