Preparation of furans by palladium-catalyzed reaction of acylchromates and propargylic tosylates

Heterocycles

Volumn 59, Issue 1, 2003, Pages 333-345

  Nakamura, Masaki ^a   Yamane, Motoki ^a   Sakurai, Hidehiro ^a,b   Narasaka, Koichi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 PROPADIENYL KETONE; 1,2 PROPADIENYLPALLADIUM COMPLEX; ACYLCHROMATE DERIVATIVE; CHROMIC ACID; FURAN DERIVATIVE; KETONE DERIVATIVE; PALLADIUM; PALLADIUM COMPLEX; PROPARGYLIC TOSYLATE; TOLUENESULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; COMPLEX FORMATION; OXIDATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0037229069     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-02-s44     Document Type: Article

References (42)

1. A review of allyl and propargyl palladium complexes; H. Kurosawa and S. Ogoshi, Bull. Chem. Soc. Jpn., 1998, 71, 973.
2. Reviews of the palladium-catalyzed coupling reaction using propargyl compounds; J. Tsuji and T. Mandai, Angew. Chem., Int. Ed. Engl., 1995, 34, 2589;
3. J. Tsuji, "Palladium Reagents and Catalysts," Wiley, Chichester 1995, pp. 453-471.
4. H. Sakurai, K. Tanabe, and K. Narasaka, Chem. Lett., 1999, 309.
5. H. Sakurai, K. Tanabe, and K. Narasaka, Chem. Lett., 2000, 168.
6. 3) δ = 23.1, 29.6, 55.4, 88.7, 97.0, 114.2, 121.7, 129.1, 163.1, 206.5; C. M. Brennan, C. D. Johnson, and P. D. McDonnell, J. Chem. Soc., Perkin Trans. H, 1989, 957.
7. 3) δ = 23.1, 29.6, 55.4, 88.7, 97.0, 114.2, 121.7, 129.1, 163.1, 206.5; C. M. Brennan, C. D. Johnson, and P. D. McDonnell, J. Chem. Soc., Perkin Trans. H, 1989, 957.
8. G. B. Bodner, S. B. Kahl, K. Bork, B. N. Storhoff, J. E. Wuller, and L. T. Todd, Inorg. Chem., 1973, 12, 1071.
9. 5 (M=Cr, Mo, W) driven cyclizations of alkynic compounds have been reported. See, K. H. Dötz and W. Sturm, Organometallics, 1987, 6, 1424; F. E. McDonald, C. C. Schultz, and A. K. Chatterjee, Organometallics, 1995, 14, 3628; F. E. McDonald and M. M. Gleason, J. Am. Chem. Soc., 1996, 118, 6648; F. E. McDonald and T. O. Olson, Tetrahedron Lett., 1997, 38, 7687; K. Maeyama and N. Iwasawa, J. Org. Chem., 1999, 64, 1344; K. Ohe, K. Miki, T. Yokoi, F. Nishino, and S. Uemura, Organometallics, 2000, 19, 5525.
10. 5 (M=Cr, Mo, W) driven cyclizations of alkynic compounds have been reported. See, K. H. Dötz and W. Sturm, Organometallics, 1987, 6, 1424; F. E. McDonald, C. C. Schultz, and A. K. Chatterjee, Organometallics, 1995, 14, 3628; F. E. McDonald and M. M. Gleason, J. Am. Chem. Soc., 1996, 118, 6648; F. E. McDonald and T. O. Olson, Tetrahedron Lett., 1997, 38, 7687; K. Maeyama and N. Iwasawa, J. Org. Chem., 1999, 64, 1344; K. Ohe, K. Miki, T. Yokoi, F. Nishino, and S. Uemura, Organometallics, 2000, 19, 5525.
11. 5 (M=Cr, Mo, W) driven cyclizations of alkynic compounds have been reported. See, K. H. Dötz and W. Sturm, Organometallics, 1987, 6, 1424; F. E. McDonald, C. C. Schultz, and A. K. Chatterjee, Organometallics, 1995, 14, 3628; F. E. McDonald and M. M. Gleason, J. Am. Chem. Soc., 1996, 118, 6648; F. E. McDonald and T. O. Olson, Tetrahedron Lett., 1997, 38, 7687; K. Maeyama and N. Iwasawa, J. Org. Chem., 1999, 64, 1344; K. Ohe, K. Miki, T. Yokoi, F. Nishino, and S. Uemura, Organometallics, 2000, 19, 5525.
12. 5 (M=Cr, Mo, W) driven cyclizations of alkynic compounds have been reported. See, K. H. Dötz and W. Sturm, Organometallics, 1987, 6, 1424; F. E. McDonald, C. C. Schultz, and A. K. Chatterjee, Organometallics, 1995, 14, 3628; F. E. McDonald and M. M. Gleason, J. Am. Chem. Soc., 1996, 118, 6648; F. E. McDonald and T. O. Olson, Tetrahedron Lett., 1997, 38, 7687; K. Maeyama and N. Iwasawa, J. Org. Chem., 1999, 64, 1344; K. Ohe, K. Miki, T. Yokoi, F. Nishino, and S. Uemura, Organometallics, 2000, 19, 5525.
13. 5 (M=Cr, Mo, W) driven cyclizations of alkynic compounds have been reported. See, K. H. Dötz and W. Sturm, Organometallics, 1987, 6, 1424; F. E. McDonald, C. C. Schultz, and A. K. Chatterjee, Organometallics, 1995, 14, 3628; F. E. McDonald and M. M. Gleason, J. Am. Chem. Soc., 1996, 118, 6648; F. E. McDonald and T. O. Olson, Tetrahedron Lett., 1997, 38, 7687; K. Maeyama and N. Iwasawa, J. Org. Chem., 1999, 64, 1344; K. Ohe, K. Miki, T. Yokoi, F. Nishino, and S. Uemura, Organometallics, 2000, 19, 5525.
14. 5 (M=Cr, Mo, W) driven cyclizations of alkynic compounds have been reported. See, K. H. Dötz and W. Sturm, Organometallics, 1987, 6, 1424; F. E. McDonald, C. C. Schultz, and A. K. Chatterjee, Organometallics, 1995, 14, 3628; F. E. McDonald and M. M. Gleason, J. Am. Chem. Soc., 1996, 118, 6648; F. E. McDonald and T. O. Olson, Tetrahedron Lett., 1997, 38, 7687; K. Maeyama and N. Iwasawa, J. Org. Chem., 1999, 64, 1344; K. Ohe, K. Miki, T. Yokoi, F. Nishino, and S. Uemura, Organometallics, 2000, 19, 5525.
15. Transition metal-catalyzed furan formation from 1,2-propadienyl ketone; J. M. Marshall and E. D. Robinson, J. Org. Chem., 1990, 55, 3450; J. M. Marshall and X.-J. Wang, J. Org. Chem., 1991, 56, 960; A. S. K. Hashmi, L. Schwarz, J.-H. Choi, and T. M. Frost, Angew. Chem., Int. Ed., 2000, 39, 2285; A. V. Kel'in and V. Gevorgyon, J. Org. Chem., 2002, 67, 95.
16. Transition metal-catalyzed furan formation from 1,2-propadienyl ketone; J. M. Marshall and E. D. Robinson, J. Org. Chem., 1990, 55, 3450; J. M. Marshall and X.-J. Wang, J. Org. Chem., 1991, 56, 960; A. S. K. Hashmi, L. Schwarz, J.-H. Choi, and T. M. Frost, Angew. Chem., Int. Ed., 2000, 39, 2285; A. V. Kel'in and V. Gevorgyon, J. Org. Chem., 2002, 67, 95.
17. Transition metal-catalyzed furan formation from 1,2-propadienyl ketone; J. M. Marshall and E. D. Robinson, J. Org. Chem., 1990, 55, 3450; J. M. Marshall and X.-J. Wang, J. Org. Chem., 1991, 56, 960; A. S. K. Hashmi, L. Schwarz, J.-H. Choi, and T. M. Frost, Angew. Chem., Int. Ed., 2000, 39, 2285; A. V. Kel'in and V. Gevorgyon, J. Org. Chem., 2002, 67, 95.
18. Transition metal-catalyzed furan formation from 1,2-propadienyl ketone; J. M. Marshall and E. D. Robinson, J. Org. Chem., 1990, 55, 3450; J. M. Marshall and X.-J. Wang, J. Org. Chem., 1991, 56, 960; A. S. K. Hashmi, L. Schwarz, J.-H. Choi, and T. M. Frost, Angew. Chem., Int. Ed., 2000, 39, 2285; A. V. Kel'in and V. Gevorgyon, J. Org. Chem., 2002, 67, 95.
19. A. S. K. Hashmi, T. L. Ruppert, T. Knöfel, and J. W. Bats, J. Org. Chem., 1997, 62, 7295.
20. C. P. Casey and W. R. Brunsvold, Inorg. Chem., 1977, 16, 391; F. E. McDonald, C. B. Connolly, M. M. Gleason, T. B. Towne, and K. D. Treiber, J. Org. Chem., 1993, 58, 6952.
21. C. P. Casey and W. R. Brunsvold, Inorg. Chem., 1977, 16, 391; F. E. McDonald, C. B. Connolly, M. M. Gleason, T. B. Towne, and K. D. Treiber, J. Org. Chem., 1993, 58, 6952.
22. J. M. Maher, R. P. Beatty, and N. J. Cooper, Organometallics, 1987, 4, 1354.
23. F. Moulin, Helv. Chim. Acta, 1951, 34, 2416; V. J. Shiner Jr. and J. W. Wilson, J. Am. Chem. Soc., 1962, 84, 2406.
24. F. Moulin, Helv. Chim. Acta, 1951, 34, 2416; V. J. Shiner Jr. and J. W. Wilson, J. Am. Chem. Soc., 1962, 84, 2406.
25. P. Lauger, M. Prost, and R. Charlier, Helv. Chim. Acta, 1959, 42, 2379.
26. M.-L. Roumestant and J. Gore, Bull. Soc. Chim. Fr., 1972, 2, 591.
27. N. S. True and R. K. Bohn, J. Am. Chem. Soc., 1977, 99, 3575.
28. N. Greeves and J. S. Torode, Synthesis, 1993, 1109.
29. G. A. Russel, P. Negoviwatchai, and Y. W. Wu, J. Am. Chem. Soc., 1989, 111, 4921.
30. E. O. Fischer and A. Massböl, Chem. Ber., 1967, 100, 2445.
31. A. Pelter, M. Rowlands, and G. Clements, Synthesis, 1987, 51.
32. S. P. Tanis, M. V. Deaton, L. A. Dixon, M. C. McMills, J. W. Raggon, and M. A. Collins, J. Org. Chem., 1998, 63, 6914.
33. Y. L. Pascal, Ann. Chim., 1968, 3, 245.
34. L. Bhat, H. Ila, and H. Junjappa, J. Chem. Soc., Perkin Trans. 1, 1994, 1749.
35. B. Guizardi, M. Mella, M. Fagnoni, and A. Albini, Tetrahedron, 2000, 56, 9383.
36. A. W. Johnson, J. Chem. Soc., 1946, 895; J. R. Beadle, S. H. Korzeniowski, D. E. Rosenberg, B. J. Garcia-Slanga, and G. W. Gokel, J. Org. Chem., 1984, 49, 1594.
37. A. W. Johnson, J. Chem. Soc., 1946, 895; J. R. Beadle, S. H. Korzeniowski, D. E. Rosenberg, B. J. Garcia-Slanga, and G. W. Gokel, J. Org. Chem., 1984, 49, 1594.
38. J. B. Baudin, S. A. Julia, and R. Lome, Bull. Soc. Chim. Fr., 1992, 129, 440; S. Holand, F. Mercier, N. L. Goff, and R. Epsztein, Bull. Soc. Chim. Fr., 1972, 4357.
39. J. B. Baudin, S. A. Julia, and R. Lome, Bull. Soc. Chim. Fr., 1992, 129, 440; S. Holand, F. Mercier, N. L. Goff, and R. Epsztein, Bull. Soc. Chim. Fr., 1972, 4357.
40. G. C. R. Ellis-Davies, A. Gilbert, J. V. Warrington, and D. L. Westover, J. Photochem., 1984, 27, 259.
41. M. Kato and I. Kuwajima, Bull. Chem. Soc. Jpn., 1984, 57, 827.
42. A. Miyamoto, C. Kumaki, H. Irikawa, and Y. Okumura, Rep. Fac. Sci. Shizuoka Univ., 1994, 28, 61 (Chem. Abstr., 1994, 121, 8640w).