Stereoselective syntheses of (E)- and (Z)-1-arylalk-3-en-1-ynes and (E,E)-, (Z,E)-, (E,Z)-, and (Z,Z)-alka-1,5-dien-3-ynes via a one-pot multicomponent coupling reaction

Synthesis

Volumn , Issue 12, 2005, Pages 1991-2007

  Hoshi, Masayuki ^a   Nakayabu, Hidenori ^a   Shirakawa, Kazuya ^a  

^a KITAMI INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

(trimethylsilyl)ethynyl bromide; 1 Arylalk 3 en 1 yne; Alka 1,5 dien 3 yne; Alkenylborane; Cross coupling

Indexed keywords

CATALYSIS; CATALYST SELECTIVITY; ISOMERS; REACTION KINETICS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

(TRIMETHYLSILYL) ETHYNYL BROMIDE; 1-ARYLALK-3-EN-1-YNE; ALKA-1,5-DIEN-3-YNE; ALKENYLBORANE; CROSS-COUPLING;

NITROGEN;

1 (1 NAPHTHYL)OCT 3 EN 1 YNE; 1 (2 ISOPROPYLPHENYL)OCT 3 EN 1 YNE; 1 (2 METHYLPHENYL)OCT 3 EN 1 YNE; 1 (2 THIENYL)OCT 3 EN 1 YNE; 1 (3 PYRIDYL)OCT 3 EN 1 YNE; 1 (4 ACETOXYPHENYL)OCT 3 EN 1 YNE; 1 (4 AMINOPHENYL)OCT 3 EN 1 YNE; 1 (4 BROMOPHENYL)OCT 3 EN 1 YNE; 1 (4 METHOXYPHENYL)OCT 3 EN 1 YNE; 1 (4 NITROPHENYL)OCT 3 EN 1 YNE; 1 (CYCLOHEX 1 ENYL) 4 PHENYLBUT 1 EN 3 YNE; 1 PHENYL 3 PROPYLHEPT 3 EN 1 YNE; 1 PHENYLDEC 3 EN 1 YNE; 1,4 DIPHENYLBUT 1 EN 3 YNE; 5,5 DIMETHYL 1 PHENYLHEX 3 EN 1 YNE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CROSS COUPLING REACTION; GEOMETRY; ISOMER; SONOGASHIRA REACTION; STEREOCHEMISTRY; SUZUKI REACTION; SYNTHESIS;

EID: 23744466982     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-869955     Document Type: Article

References (92)

1. (a) Kusumi, T.; Ohtani, I.; Nishiyama, K.; Kakisawa, H. Tetrahedron Lett. 1987, 28, 3981.
2. (b) Graham, A. E.; McKerrecher, D.; Davies, D. H.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37, 7445.
3. (c) Miller, M. W.; Johnson, C. R. J. Org. Chem. 1997, 62, 1582.
4. (d) Yoshimura, F.; Kawata, S.; Hirama, M. Tetrahedron Lett. 1999, 40, 8281.
5. (e) Ohta, T.; Uwai, K.; Kikuchi, R.; Nozoe, S.; Oshima, Y.; Sasaki, K.; Yoshizaki, F. Tetrahedron 1999, 55, 12087.
6. (f) Paterson, I.; Davies, R. D. M.; Marquez, R. Angew. Chem. Int. Ed. 2001, 40, 603.
7. (g) Organ, M. G.; Ghasemi, H. J. Org. Chem. 2004, 69, 695.
8. (a) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387; and references cited therein.
9. (b) Maier, M. E. Synlett 1995, 13; and references cited therein.
10. (c) Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453; and references cited therein.
11. (d) Maier, M. E.; Boße, F.; Niestroj, A. J. Eur. J. Org. Chem. 1999, 1.
12. (a) Martin, R. E.; Diederich, F. Angew. Chem. Int. Ed. 1999, 38, 1350; and references cited therein.
13. (b) Hynd, G.; Jones, G. B.; Plourde, G. W. II; Wright, J. M. Tetrahedron Lett. 1999, 40, 4481.
14. (c) Tour, J. M. Acc. Chem. Res. 2000, 33, 791; and references cited therein.
15. (d) Bunz, U. H. F. Chem. Rev. 2000, 100, 1605; and references cited therein.
16. (e) Siemsen, P.; Livingston, R. C.; Diederich, F. Angew. Chem. Int. Ed. 2000, 39, 2632; and references cited therein.
17. (f) Shimada, S.; Masaki, A.; Hayamizu, K.; Matsuda, H.; Okada, S.; Nakanishi, H. Chem. Lett. 2000, 1128.
18. (g) Collins, S. K.; Yap, G. P. A.; Fallis, A. G. Org. Lett. 2000, 2, 3189.
19. (h) Ciulei, S. C.; Tykwinski, R. R. Org. Lett. 2000, 2, 3607.
20. (i) Schmittel, M.; Michel, C.; Wiegrefe, A.; Kalsani, V. Synthesis 2001, 1561.
21. (j) Heuft, M. A.; Collins, S. K.; Yap, G. P. A.; Fallis, A. G. Org. Lett. 2001, 3, 2883.
22. (k) Nielsen, M. B.; Moonen, N. N. P.; Boudon, C.; Gisselbrecht, J.-P.; Seiler, P.; Gross, M.; Diederich, F. Chem. Commun. 2001, 1848.
23. (l) Rodriguez, J. G.; Tejedor, J. L. J. Org. Chem. 2002, 67, 7631.
24. (m) Rodriguez, J. G.; Tejedor, J. L. Tetrahedron Lett. 2003, 44, 2691.
25. (n) Kaafarani, B. R.; Wex, B.; Wang, F.; Catanescu, O.; Chien, L. C.; Neckers, D. C. J. Org. Chem. 2003, 68, 5377.
26. (o) Rodriguez, J. G.; Esquivias, J.; Lafuente, A.; Diaz, C. J. Org. Chem. 2003, 68, 8120.
27. (p) Chanteau, S. H.; Tour, J. M. J. Org. Chem. 2003, 68, 8750.
28. (q) Takayama, Y.; Delas, C.; Muraoka, K.; Uemura, M.; Sato, F. J. Am. Chem. Soc. 2003, 125, 14163.
29. (r) Wilson, J. N.; Josowicz, M.; Wang, Y.; Bunz, U. H. F. Chem. Commun. 2003, 2962.
30. (s) Kozaki, M.; Okada, K. Org. Lett. 2004, 6, 485.
31. (t) Shirai, Y.; Zhao, Y.; Cheng, L.; Tour, J. M. Org. Lett. 2004, 6, 2129.
32. Nagata, T.; Ando, Y.; Hirota, A. Biosci. Biotechnol. Biochem. 1992, 56, 810.
33. Garlaschelli, L.; Magistrali, E.; Vidari, G.; Zuffardi, O. Tetrahedron Lett. 1995, 36, 5633.
34. Müller, H.; Schmidt, C.; Kehr, S.; Hagedorn, M. Macromol. Rapid Commun. 2000, 21, 449.
35. Sonoda, M.; Itahashi, K.; Tobe, Y. Tetrahedron Lett. 2002, 43, 5269.
36. (a) Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998.
37. (b) Tsuji, J. Transition Metal Reagents and Catalysts: Innovations in Organic Synthesis; Wiley: Chichester, 2000.
38. (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
39. (b) Suzuki, A. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998.
40. (c) Suzuki, A. J. Organomet. Chem. 1999, 576, 147.
41. (a) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467.
42. (b) Sonogashira, K. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998.
43. (c) Sonogashira, K. J. Organomet. Chem. 2002, 653, 46.
44. Hoshi, M.; Shirakawa, K. Synlett 2002, 1101.
45. 11
46. The amount of 1 M NaOMe could be reduced to three-quarters with about the same yield of product as the previous report: Hoshi, M.; Nakayabu, H.; Shirakawa, K. unpublished results.
47. (a) Mori, A.; Mohamed Ahmed, M. S.; Sekiguchi, A.; Masui, K.; Koike, T. Chem. Lett. 2002, 756.
48. (b) Mori, A.; Shimada, T.; Kondo, T.; Sekiguchi, A. Synlett 2001, 649.
49. For examples, see: (a) Jun, C.-H.; Lu, Z.; Crabtree, R. H. Tetrahedron Lett. 1992, 33, 7119.
50. (b) Yi, C. S.; Liu, N. Organometallics 1996, 15, 3968.
51. (c) Slugovc, C.; Mereiter, K.; Zobetz, E.; Schmid, R.; Kirchner, K. Organometallics 1996, 15, 5275.
52. (d) Yi, C. S.; Liu, N.; Rheingold, A. L.; Liable-Sands, L. M. Organometallics 1997, 16, 3910.
53. (e) Ohmura, T.; Yorozuya, S.; Yamamoto, Y.; Miyaura, N. Organometallics 2000, 19, 365.
54. (f) Rubina, M.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 11107.
55. (g) Yang, C.; Nolan, S. P. J. Org. Chem. 2002, 67, 591.
56. (h) Nishiura, M.; Hou, Z.; Wakatsuki, Y.; Yamaki, T.; Miyamoto, T. J. Am. Chem. Soc. 2003, 125, 1184.
57. (i) Wang, C.-Y.; Su, H.; Yang, D.-Y. Synlett 2004, 561.
58. (j) Tazelaar, C. G. J.; Bambirra, S.; Van Leusen, D.; Meetsma, A.; Hessen, B.; Teuben, J. H. Organometallics 2004, 23, 936.
59. (k) Komeyama, K.; Takehira, K.; Takaki, K. Synthesis 2004, 1062.
60. (a) Akita, M.; Yasuda, H.; Nakamura, A. Bull. Chem. Soc. Jpn. 1984, 57, 480.
61. (b) Trost, B. M.; Sorum, M. T.; Chan, C.; Harms, A. E.; Rühter, G. J. Am. Chem. Soc. 1997, 119, 698.
62. (c) Chen, L.; Li, C.-J. Tetrahedron Lett. 2004, 45, 2771.
63. For examples, see: (a) Miyaura, N.; Yamada, K.; Suginome, H.; Suzuki, A. J. Am. Chem. Soc. 1985, 107, 972.
64. (b) Hoshi, M.; Masuda, Y.; Arase, A. Bull. Chem. Soc. Jpn. 1983, 56, 2855.
65. (c) Hara, R.; Liu, Y.; Sun, W.-H.; Takahashi, T. Tetrahedron Lett. 1997, 38, 4103.
66. (d) Masuda, Y.; Murata, M.; Sato, K.; Watanabe, S. Chem. Commun. 1998, 807.
67. (e) Zeni, G.; Alves, D.; Pena, J. M.; Braga, A. L.; Stefani, H. A.; Nogueira, C. W. Org. Biomol. Chem. 2004, 2, 803.
68. (f) Raminelli, C.; Prechtl, M. H. G.; Santos, L. S.; Eberlin, M. N.; Comasseto, J. V. Organometallics 2004, 23, 3990.
69. (g) Raminelli, C.; Gargalaka, J. Jr.; Silveira, C. C.; Comasseto, J. V. Tetrahedron Lett. 2004, 45, 4927.
70. (h) Alami, M.; Ramiandrasoa, P.; Cahiez, G. Synlett 1998, 325.
71. (i) Choukroun, R.; Zhao, J.; Lorber, C.; Cassoux, P.; Donnadieu, B. Chem. Commun. 2000, 1511.
72. (j) Kleijn, H.; Tigchelaar, M.; Meijer, J.; Vermeer, P. Recl. Trav. Chim. Pays-Bas 1981, 100, 337.
73. (k) Yoshimatsu, M.; Yamada, H.; Shimizu, H.; Kataoka, T. J. Chem. Soc., Chem. Commun. 1994, 2107.
74. Johnson, C. R.; Braun, M. P. J. Am. Chem. Soc. 1993, 115, 11014.
75. Hayashi, T.; Konishi, M.; Kobori, Y.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158.
76. Negishi, E.; Williams, R. M.; Lew, G.; Yoshida, T. J. Organomet. Chem. 1975, 92, C4.
77. (a) Amatore, C.; Azzabi, M.; Jutand, A. J. Organomet. Chem. 1989, 363, C41.
78. (b) Amatore, C.; Azzabi, M.; Jutand, A. J. Am. Chem. Soc. 1991, 113, 8375.
79. (a) Negishi, E.; Takahashi, T.; Akiyoshi, K. J. Chem. Soc., Chem. Commun. 1986, 1338.
80. (b) Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3033.
81. Hatanaka, Y.; Matsui, K.; Hiyama, T. Tetrahedron Lett. 1989, 30, 2403.
82. (a) Carpita, A.; Neri, D.; Rossi, R. Gazz. Chim. Ital. 1987, 117, 481.
83. (b) Andreint, B. P.; Benetti, M.; Carpita, A.; Rossi, R. Tetrahedron 1987, 43, 4591.
84. Tellier, F.; Descoins, C.; Sauvêtre, R. Tetrahedron 1991, 47, 7767.
85. Hofmeister, H.; Annen, K.; Laurent, H.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1984, 23, 727.
86. Southwick, P. L.; Kirchiner, J. R. J. Org. Chem. 1962, 27, 3305.
87. (a) Zweifel, G.; Whitney, C. C. J. Am. Chem. Soc. 1967, 89, 2753.
88. (b) Hoshi, M.; Shirakawa, K. Chem. Commun. 2002, 2146.
89. Hoshi, M.; Arase, A. Synth. Commun. 1997, 27, 567.
90. (a) Zweifel, G.; Brown, H. C. Org. React. 1963, 13, 1.
91. (b) Brown, H. C. Organic Syntheses via Boranes; Wiley-Interscience: New York, 1975.
92. The work-up procedure should be carried out at or below room temperature in order to avoid any decomposition of the product.