Palladium-catalyzed coupling reaction of salicylaldehydes with aryl iodides via cleavage of the aldehyde C-H bond

Chemistry Letters

Volumn , Issue 9, 1996, Pages 823-824

  Satoh, Tetsuya ^a   Itaya, Tomoaki ^a   Miura, Masahiro ^a   Nomura, Masakatsu ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0030355414     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1996.823     Document Type: Article

References (28)

1. G. W. Parshall, Acc. Chem. Res, 8, 113 (1975); G. W. Parshall, CHEMTECH, 1984, 628; A. D. Ryabov, Chem. Rev, 90, 403 (1990).
2. G. W. Parshall, Acc. Chem. Res, 8, 113 (1975); G. W. Parshall, CHEMTECH, 1984, 628; A. D. Ryabov, Chem. Rev, 90, 403 (1990).
3. G. W. Parshall, Acc. Chem. Res, 8, 113 (1975); G. W. Parshall, CHEMTECH, 1984, 628; A. D. Ryabov, Chem. Rev, 90, 403 (1990).
4. P. Hong, H. Yamazaki, K. Sonogashira, and N. Hagihara, Chem. Lett., 1978, 535; P. Hong and H. Yamazaki, Chem. Lett., 1979, 1335; S.-I. Murahashi, T. Naota, and H. Taki, J. Chem. Soc., Chem. Commun., 1985, 613; W. D. Jones and W. P. Kosar, J. Am. Chem. Soc., 108, 5640 (1986); L. N. Lewis and J. F. Smith, J. Am. Chem. Soc., 108, 2728 (1986); R. F. Jordan and D.F. Taylor, J. Am. Chem. Soc., 111, 778 (1989); M. Tanaka, CHEMTECH, 19, 59 (1989); Y. Fujiwara, T. Jintoku, and K. Takaki, CHEMTECH, 20, 636 (1990); E. J. Moore, W. R. Pretzer, T. J. O'Connell, J. Harris, L. LaBounty, L. Chou, and S. S. Grimmer, J. Am. Chem. Soc., 114, 5888 (1992); G. Dyker, Angew. Chem., Int. Ed. Engl., 33, 103 (1994).
5. P. Hong, H. Yamazaki, K. Sonogashira, and N. Hagihara, Chem. Lett., 1978, 535; P. Hong and H. Yamazaki, Chem. Lett., 1979, 1335; S.-I. Murahashi, T. Naota, and H. Taki, J. Chem. Soc., Chem. Commun., 1985, 613; W. D. Jones and W. P. Kosar, J. Am. Chem. Soc., 108, 5640 (1986); L. N. Lewis and J. F. Smith, J. Am. Chem. Soc., 108, 2728 (1986); R. F. Jordan and D.F. Taylor, J. Am. Chem. Soc., 111, 778 (1989); M. Tanaka, CHEMTECH, 19, 59 (1989); Y. Fujiwara, T. Jintoku, and K. Takaki, CHEMTECH, 20, 636 (1990); E. J. Moore, W. R. Pretzer, T. J. O'Connell, J. Harris, L. LaBounty, L. Chou, and S. S. Grimmer, J. Am. Chem. Soc., 114, 5888 (1992); G. Dyker, Angew. Chem., Int. Ed. Engl., 33, 103 (1994).
6. P. Hong, H. Yamazaki, K. Sonogashira, and N. Hagihara, Chem. Lett., 1978, 535; P. Hong and H. Yamazaki, Chem. Lett., 1979, 1335; S.-I. Murahashi, T. Naota, and H. Taki, J. Chem. Soc., Chem. Commun., 1985, 613; W. D. Jones and W. P. Kosar, J. Am. Chem. Soc., 108, 5640 (1986); L. N. Lewis and J. F. Smith, J. Am. Chem. Soc., 108, 2728 (1986); R. F. Jordan and D.F. Taylor, J. Am. Chem. Soc., 111, 778 (1989); M. Tanaka, CHEMTECH, 19, 59 (1989); Y. Fujiwara, T. Jintoku, and K. Takaki, CHEMTECH, 20, 636 (1990); E. J. Moore, W. R. Pretzer, T. J. O'Connell, J. Harris, L. LaBounty, L. Chou, and S. S. Grimmer, J. Am. Chem. Soc., 114, 5888 (1992); G. Dyker, Angew. Chem., Int. Ed. Engl., 33, 103 (1994).
7. P. Hong, H. Yamazaki, K. Sonogashira, and N. Hagihara, Chem. Lett., 1978, 535; P. Hong and H. Yamazaki, Chem. Lett., 1979, 1335; S.-I. Murahashi, T. Naota, and H. Taki, J. Chem. Soc., Chem. Commun., 1985, 613; W. D. Jones and W. P. Kosar, J. Am. Chem. Soc., 108, 5640 (1986); L. N. Lewis and J. F. Smith, J. Am. Chem. Soc., 108, 2728 (1986); R. F. Jordan and D.F. Taylor, J. Am. Chem. Soc., 111, 778 (1989); M. Tanaka, CHEMTECH, 19, 59 (1989); Y. Fujiwara, T. Jintoku, and K. Takaki, CHEMTECH, 20, 636 (1990); E. J. Moore, W. R. Pretzer, T. J. O'Connell, J. Harris, L. LaBounty, L. Chou, and S. S. Grimmer, J. Am. Chem. Soc., 114, 5888 (1992); G. Dyker, Angew. Chem., Int. Ed. Engl., 33, 103 (1994).
8. P. Hong, H. Yamazaki, K. Sonogashira, and N. Hagihara, Chem. Lett., 1978, 535; P. Hong and H. Yamazaki, Chem. Lett., 1979, 1335; S.-I. Murahashi, T. Naota, and H. Taki, J. Chem. Soc., Chem. Commun., 1985, 613; W. D. Jones and W. P. Kosar, J. Am. Chem. Soc., 108, 5640 (1986); L. N. Lewis and J. F. Smith, J. Am. Chem. Soc., 108, 2728 (1986); R. F. Jordan and D.F. Taylor, J. Am. Chem. Soc., 111, 778 (1989); M. Tanaka, CHEMTECH, 19, 59 (1989); Y. Fujiwara, T. Jintoku, and K. Takaki, CHEMTECH, 20, 636 (1990); E. J. Moore, W. R. Pretzer, T. J. O'Connell, J. Harris, L. LaBounty, L. Chou, and S. S. Grimmer, J. Am. Chem. Soc., 114, 5888 (1992); G. Dyker, Angew. Chem., Int. Ed. Engl., 33, 103 (1994).
9. P. Hong, H. Yamazaki, K. Sonogashira, and N. Hagihara, Chem. Lett., 1978, 535; P. Hong and H. Yamazaki, Chem. Lett., 1979, 1335; S.-I. Murahashi, T. Naota, and H. Taki, J. Chem. Soc., Chem. Commun., 1985, 613; W. D. Jones and W. P. Kosar, J. Am. Chem. Soc., 108, 5640 (1986); L. N. Lewis and J. F. Smith, J. Am. Chem. Soc., 108, 2728 (1986); R. F. Jordan and D.F. Taylor, J. Am. Chem. Soc., 111, 778 (1989); M. Tanaka, CHEMTECH, 19, 59 (1989); Y. Fujiwara, T. Jintoku, and K. Takaki, CHEMTECH, 20, 636 (1990); E. J. Moore, W. R. Pretzer, T. J. O'Connell, J. Harris, L. LaBounty, L. Chou, and S. S. Grimmer, J. Am. Chem. Soc., 114, 5888 (1992); G. Dyker, Angew. Chem., Int. Ed. Engl., 33, 103 (1994).
10. P. Hong, H. Yamazaki, K. Sonogashira, and N. Hagihara, Chem. Lett., 1978, 535; P. Hong and H. Yamazaki, Chem. Lett., 1979, 1335; S.-I. Murahashi, T. Naota, and H. Taki, J. Chem. Soc., Chem. Commun., 1985, 613; W. D. Jones and W. P. Kosar, J. Am. Chem. Soc., 108, 5640 (1986); L. N. Lewis and J. F. Smith, J. Am. Chem. Soc., 108, 2728 (1986); R. F. Jordan and D.F. Taylor, J. Am. Chem. Soc., 111, 778 (1989); M. Tanaka, CHEMTECH, 19, 59 (1989); Y. Fujiwara, T. Jintoku, and K. Takaki, CHEMTECH, 20, 636 (1990); E. J. Moore, W. R. Pretzer, T. J. O'Connell, J. Harris, L. LaBounty, L. Chou, and S. S. Grimmer, J. Am. Chem. Soc., 114, 5888 (1992); G. Dyker, Angew. Chem., Int. Ed. Engl., 33, 103 (1994).
11. P. Hong, H. Yamazaki, K. Sonogashira, and N. Hagihara, Chem. Lett., 1978, 535; P. Hong and H. Yamazaki, Chem. Lett., 1979, 1335; S.-I. Murahashi, T. Naota, and H. Taki, J. Chem. Soc., Chem. Commun., 1985, 613; W. D. Jones and W. P. Kosar, J. Am. Chem. Soc., 108, 5640 (1986); L. N. Lewis and J. F. Smith, J. Am. Chem. Soc., 108, 2728 (1986); R. F. Jordan and D.F. Taylor, J. Am. Chem. Soc., 111, 778 (1989); M. Tanaka, CHEMTECH, 19, 59 (1989); Y. Fujiwara, T. Jintoku, and K. Takaki, CHEMTECH, 20, 636 (1990); E. J. Moore, W. R. Pretzer, T. J. O'Connell, J. Harris, L. LaBounty, L. Chou, and S. S. Grimmer, J. Am. Chem. Soc., 114, 5888 (1992); G. Dyker, Angew. Chem., Int. Ed. Engl., 33, 103 (1994).
12. P. Hong, H. Yamazaki, K. Sonogashira, and N. Hagihara, Chem. Lett., 1978, 535; P. Hong and H. Yamazaki, Chem. Lett., 1979, 1335; S.-I. Murahashi, T. Naota, and H. Taki, J. Chem. Soc., Chem. Commun., 1985, 613; W. D. Jones and W. P. Kosar, J. Am. Chem. Soc., 108, 5640 (1986); L. N. Lewis and J. F. Smith, J. Am. Chem. Soc., 108, 2728 (1986); R. F. Jordan and D.F. Taylor, J. Am. Chem. Soc., 111, 778 (1989); M. Tanaka, CHEMTECH, 19, 59 (1989); Y. Fujiwara, T. Jintoku, and K. Takaki, CHEMTECH, 20, 636 (1990); E. J. Moore, W. R. Pretzer, T. J. O'Connell, J. Harris, L. LaBounty, L. Chou, and S. S. Grimmer, J. Am. Chem. Soc., 114, 5888 (1992); G. Dyker, Angew. Chem., Int. Ed. Engl., 33, 103 (1994).
13. P. Hong, H. Yamazaki, K. Sonogashira, and N. Hagihara, Chem. Lett., 1978, 535; P. Hong and H. Yamazaki, Chem. Lett., 1979, 1335; S.-I. Murahashi, T. Naota, and H. Taki, J. Chem. Soc., Chem. Commun., 1985, 613; W. D. Jones and W. P. Kosar, J. Am. Chem. Soc., 108, 5640 (1986); L. N. Lewis and J. F. Smith, J. Am. Chem. Soc., 108, 2728 (1986); R. F. Jordan and D.F. Taylor, J. Am. Chem. Soc., 111, 778 (1989); M. Tanaka, CHEMTECH, 19, 59 (1989); Y. Fujiwara, T. Jintoku, and K. Takaki, CHEMTECH, 20, 636 (1990); E. J. Moore, W. R. Pretzer, T. J. O'Connell, J. Harris, L. LaBounty, L. Chou, and S. S. Grimmer, J. Am. Chem. Soc., 114, 5888 (1992); G. Dyker, Angew. Chem., Int. Ed. Engl., 33, 103 (1994).
14. H. M. Coloquhoun, D. J. Thompson, and M. V. Twigg "Carbonylation," Plenum Press, New York (1991), Chap. 11.
15. K. Sakai, J. Ide, O. Oda, and N. Nakamura, Tetrahedron Lett., 1972, 1287; T. B. Marder, D. Christopher Roe, and D. Milstein, Organometallics, 7, 1451 (1988); T. Kondo, M. Akazome, Y. Tsuji, and Y. Watanabe, J Org. Chem., 55, 1286 (1990); R. W. Barnhart, X. Wang, P. Noheda, S. H. Bergens, J. Whelan, and B. Bosnich, J. Am. Chem. Soc., 116, 1821 (1994).
16. K. Sakai, J. Ide, O. Oda, and N. Nakamura, Tetrahedron Lett., 1972, 1287; T. B. Marder, D. Christopher Roe, and D. Milstein, Organometallics, 7, 1451 (1988); T. Kondo, M. Akazome, Y. Tsuji, and Y. Watanabe, J Org. Chem., 55, 1286 (1990); R. W. Barnhart, X. Wang, P. Noheda, S. H. Bergens, J. Whelan, and B. Bosnich, J. Am. Chem. Soc., 116, 1821 (1994).
17. K. Sakai, J. Ide, O. Oda, and N. Nakamura, Tetrahedron Lett., 1972, 1287; T. B. Marder, D. Christopher Roe, and D. Milstein, Organometallics, 7, 1451 (1988); T. Kondo, M. Akazome, Y. Tsuji, and Y. Watanabe, J Org. Chem., 55, 1286 (1990); R. W. Barnhart, X. Wang, P. Noheda, S. H. Bergens, J. Whelan, and B. Bosnich, J. Am. Chem. Soc., 116, 1821 (1994).
18. K. Sakai, J. Ide, O. Oda, and N. Nakamura, Tetrahedron Lett., 1972, 1287; T. B. Marder, D. Christopher Roe, and D. Milstein, Organometallics, 7, 1451 (1988); T. Kondo, M. Akazome, Y. Tsuji, and Y. Watanabe, J Org. Chem., 55, 1286 (1990); R. W. Barnhart, X. Wang, P. Noheda, S. H. Bergens, J. Whelan, and B. Bosnich, J. Am. Chem. Soc., 116, 1821 (1994).
19. S. Murai, F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, and N. Chalani, Nature (London), 366, 529 (1993); F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M Sonoda, N. Chatani, and S. Murai, Bull. Chem. Soc. Jpn., 68, 62 (1995); S. Murai, J. Synth. Org. Chem. Jpn., 54, 992 (1994) and references therein.
20. S. Murai, F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, and N. Chalani, Nature (London), 366, 529 (1993); F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M Sonoda, N. Chatani, and S. Murai, Bull. Chem. Soc. Jpn., 68, 62 (1995); S. Murai, J. Synth. Org. Chem. Jpn., 54, 992 (1994) and references therein.
21. S. Murai, F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, and N. Chalani, Nature (London), 366, 529 (1993); F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M Sonoda, N. Chatani, and S. Murai, Bull. Chem. Soc. Jpn., 68, 62 (1995); S. Murai, J. Synth. Org. Chem. Jpn., 54, 992 (1994) and references therein.
22. Y-G. Lim, Y. H. Kim, and J.-B. Kang, J. Chem. Soc., Chem. Commun., 1994, 2267.
23. R. F. Heck, "Palladium Reagents in Organic Syntheses," Academic Press, New York (1985).
24. K. Itoh, M. Miura, and M. Nomura, Tetrahedron Lett., 1992, 5369; T. Satoh, K. Kokubo, M. Miura, and M. Nomura, Organometallics, 13, 4431 (1994); T. Satoh, T. Tsuda, Y. Kushino, M. Miura, and M. Nomura, The 70th Annual Meeting of the Chemical Society of Japan, Tokyo, 1996, Abstr., 3J215.
25. K. Itoh, M. Miura, and M. Nomura, Tetrahedron Lett., 1992, 5369; T. Satoh, K. Kokubo, M. Miura, and M. Nomura, Organometallics, 13, 4431 (1994); T. Satoh, T. Tsuda, Y. Kushino, M. Miura, and M. Nomura, The 70th Annual Meeting of the Chemical Society of Japan, Tokyo, 1996, Abstr., 3J215.
26. K. Itoh, M. Miura, and M. Nomura, Tetrahedron Lett., 1992, 5369; T. Satoh, K. Kokubo, M. Miura, and M. Nomura, Organometallics, 13, 4431 (1994); T. Satoh, T. Tsuda, Y. Kushino, M. Miura, and M. Nomura, The 70th Annual Meeting of the Chemical Society of Japan, Tokyo, 1996, Abstr., 3J215.
27. Similar mechanisms involving intramolecular oxidative addition of aldehyde C-H bond to organopalladium(II) intermediates have been recently proposed for the palladium-catalyzed reactions of o-halobenzaldehydes with alkenes and alkynes: S. K. Meegalla, N. J. Taylor, and R. Rodrigo, J. Org. Chem., 57, 2422 (1992); R. C. Larock and M. J. Doty, J. Org. Chem., 58, 4579 (1993).
28. Similar mechanisms involving intramolecular oxidative addition of aldehyde C-H bond to organopalladium(II) intermediates have been recently proposed for the palladium-catalyzed reactions of o-halobenzaldehydes with alkenes and alkynes: S. K. Meegalla, N. J. Taylor, and R. Rodrigo, J. Org. Chem., 57, 2422 (1992); R. C. Larock and M. J. Doty, J. Org. Chem., 58, 4579 (1993).