Synthesis of highly substituted 1,3-butadienes by palladium-catalyzed arylation of internal alkynes

Angewandte Chemie - International Edition

Volumn 43, Issue 38, 2004, Pages 5063-5065

  Satoh, Tetsuya ^a   Ogino, Shinji ^a   Miura, Masahiro ^a   Nomura, Masakatsu ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Alkynes; Arylation; C C coupling; Homogeneous catalysis; Palladium

Indexed keywords

BENZENE; CATALYSIS; CATALYST SELECTIVITY; CATALYSTS; PALLADIUM; SILVER; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

ALKYNES; SELECTIVE CATALYSIS;

BUTADIENE;

1,3 BUTADIENE; ALKYNE; BORONIC ACID DERIVATIVE; IODOBENZENE; PALLADIUM;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONJUGATION; REACTION ANALYSIS; RING CLOSING METATHESIS; SYNTHESIS;

ALKYNES; BUTADIENES; CATALYSIS; MOLECULAR STRUCTURE; PALLADIUM; STEREOISOMERISM;

EID: 4944233291     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200460409     Document Type: Article

References (41)

1. a) I. Marek, J. F. Normant in Metal-catalyzed Cross-coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, p. 271;
2. b) S. Bräse, A. de Meijere in Handbook of Organopalladium Chemistry for Organic Synthesis (Ed: E. Negishi), Wiley-Interscience, New York, 2002, p. 1369;
3. c) K. Fagnou, M. Lautens, Chem. Rev. 2003, 103, 169.
4. a) K. Kokubo, K. Matsumasa, M. Miura, M. Nomura, J. Org. Chem. 1996, 61, 6941;
5. b) T. Yasukawa, T. Satoh, M. Miura, M. Nomura, J. Am. Chem. Soc. 2002, 124, 12 680;
6. c) S. Kawasaki, T. Satoh, M. Miura, M. Nomura, J. Org. Chem. 2003, 68, 6836.
7. M. Kotora, H. Matsumura, G. Gao, T. Takahashi, Org. Lett. 2001, 3, 3467.
8. For examples, see: a) Y. Fujiwara, C. Jia in Handbook of Organopalladium Chemistry for Organic Synthesis (Ed.: E. Negishi), Wiley-Interscience, New York, 2002, p. 2859;
9. b) A. G. Myers, D. Tanaka, M. R. Mannion, J. Am. Chem. Soc. 2002, 124, 11250;
10. c) L. M. Klingensmith, N. E. Leadbeater, Tetrahedron Lett. 2003, 44, 765.
11. H. Oda, M. Morishita, K. Fugami, H. Sano, M. Kosugi, Chem. Lett. 1996, 811.
12. C. Broquet, H. Riviere, J. Organomet. Chem. 1982, 226, 1.
13. In contrast to the reactions with aryl metal reagents, the use of the corresponding methyl metal reagents results in 2:2 coupling to give 1,4-dimethyl-1,3-butadienes.[5,6]
14. For the homocoupling of aryl boronic acids, see: a) K. A. Smith, E. M. Campi, W. R. Jackson, S. Marcuccio, C. G. M. Naeslund, G. B. Deacon, Synlett 1997, 131;
15. b) M. S. Wong, X. L. Zhang, Tetrahedron Lett. 2001, 42, 4087;
16. c) G. W. Kabalka, L. Wang, Tetrahedron Lett. 2002, 43, 3067;
17. d) J. P. Parrish, Y. C. Jung, R. J. Floyd, K. W. Jung, Tetrahedron Lett. 2002, 43, 7899;
18. e) H. Yoshida, Y. Yamaryo, J. Ohshita, A. Kunai, Tetrahedron Lett. 2003, 44, 1541.
19. For Heck-type coupling of aryl boronic acids, see: a) C. S. Cho, S. Uemura, J. Organomet. Chem. 1994, 465, 85;
20. b) X. Du, M. Suguro, K. Hirabayashi, A. Mori, T. Nishikata, N. Hagiwara, K. Kawata, T. Okada, H. F. Wang, K. Fugami, M. Kosugi, Org. Lett. 2001, 3, 3313;
21. c) Y. C. Jung, R. K. Mishra, C. H. Yoon, K. W. Jung, Org. Lett. 2003, 5, 2231;
22. d) M. M. S. Andappan, P. Nilsson, M. Larhed, Chem. Commun. 2004, 218.
23. A 1:2 coupling of vinyl boronates with alkynes to give vinylidene cyclopentadienes has been reported.[9b]
24. C. Zhou, D. E. Emrich, R. C. Larock, Org. Lett. 2003, 5, 1579.
25. The use of tetramethyltin, acetylene dicarboxylates, and aryl iodides affords 1:2:1 coupling products: a) R. van Belzen, H. Hoffmann, C. J. Elsevier, Angew. Chem. 1997, 109, 1833; Angew. Chem. Int. Ed. Engl. 1997, 36, 1743;
26. The use of tetramethyltin, acetylene dicarboxylates, and aryl iodides affords 1:2:1 coupling products: a) R. van Belzen, H. Hoffmann, C. J. Elsevier, Angew. Chem. 1997, 109, 1833; Angew. Chem. Int. Ed. Engl. 1997, 36, 1743;
27. b) R. van Belzen, R. A. Klein, H. Kooijman, N. Veldman, A. L. Spek, C. J. Elsevier, Organometallics 1998, 17, 1812.
28. CCDC-236 664 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/ retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: (+44) 1223-336-033; or deposit@ ccdc.cam.ac.uk).
29. 2O, 3% in 1-propanol). The structure of the by-product shown below was unambiguously determined by its 2D NMR spectra and NOE experiments. A similar product is formed by the reaction of iodobenzene with 3-hexyne: G. Wu, A. L. Rheingold, S. J. Gelb, R. F. Heck, Organometallics 1987, 6, 1941.
30. Although the reason why only two molecules of the alkynes are selectively incorporated into the products is not definitive at the present stage, it may be attributed to stabilization of the dienylpalladium intermediate (C in Scheme 4) by chelation; see: X. Zeng, Q. Hu, M. Qian, E.-I. Negishi, J. Am. Chem. Soc. 2003, 125, 13 636.
31. 2O at 120 °C for 0.5 h gave predominantly diene 3a in 56% yield, along with a small amount of 4a (2%). This result indicates that the diene formation can take place on Pd and that the participation of vinyl silver(I) species cannot be excluded.
32. 2O at 120 °C for 0.5 h gave predominantly diene 3a in 56% yield, along with a small amount of 4a (2%). This result indicates that the diene formation can take place on Pd and that the participation of vinyl silver(I) species cannot be excluded.
33. G. Dyker, A. Kellner, Tetrahedron Lett. 1994, 35, 7633. Z,Z Butadienes are also known to undergo thermal isomerization to the corresponding E,E isomers via cyclobutenes: G. A. Doorakian, H. H. Freedman, J. Am. Chem. Soc. 1968, 90, 5310.
34. G. Dyker, A. Kellner, Tetrahedron Lett. 1994, 35, 7633. Z,Z Butadienes are also known to undergo thermal isomerization to the corresponding E,E isomers via cyclobutenes: G. A. Doorakian, H. H. Freedman, J. Am. Chem. Soc. 1968, 90, 5310.
35. 0 species with two alkyne molecules cannot be excluded. Both mechanisms via palladacycle[12,18a] and acyclic intermediates[18b] have been proposed for diene synthesis reactions: a) E. Shirakawa, H. Yoshida, Y. Nakao, T. Hiyama, J. Am. Chem. Soc. 1999, 121, 4290;
36. b) H. Kinoshita, T. Nakamura, H. Kakiya, H. Shinokubo, S. Matsubara, K. Oshima, Org. Lett. 2001, 3, 2521.
37. For recent papers, see: a) S. Hünig, M. Kemmer, H. Wenner, F. Barbosa, G. Gescheidt, I. F. Perepichka, P. Bäuerle, A. Emge, K. Peters, Chem. Eur. J. 2000, 6, 2618;
38. b) J.-H. Kim, S. Noh, K. Kim, S.-T. Lim, D.-M. Shin, Synth. Met. 2001, 117, 227;
39. c) T. Suzuki, H. Higuchi, M. Ohkita, T. Tsuji, Chem. Commun. 2001, 1574;
40. d) R. Davis, V. A. Mallia, S. Das, Chem. Mater. 2003, 15, 1057;
41. e) J. L. Gage, H. A. Kirst, D. O'Neil, B. A. David, C. K. Smith II, S. A. Naylor, Bioorg. Med. Chem. 2003, 11, 4083.