Cyclization-carbonylation-cyclization coupling reactions of propargyl acetates and amides with palladium(II)-bisoxazoline catalysts

Angewandte Chemie - International Edition

Volumn 50, Issue 17, 2011, Pages 3912-3915

  Yasuhara, Sumie ^a   Sasa, Makiko ^a   Kusakabe, Taichi ^a   Takayama, Hiroyuki ^b   Kimura, Masayuki ^b   Mochida, Tomoyuki ^c   Kato, Keisuke ^a  

^a TOHO UNIVERSITY   (Japan)

^b NIHON PHARMACEUTICAL UNIVERSITY   (Japan)

^c KOBE UNIVERSITY   (Japan)

Author keywords

alkynes; bisoxazoline ligands; C O coupling; carbonylation; palladium

Indexed keywords

ALKYNES; BIS-OXAZOLINE; C-O COUPLING; CYCLIZATION-COUPLING REACTION; FURANONES; HETEROCYCLIC GROUPS; PROPARGYL; TRIFLUOROACETATES;

ACETYLENE; AMIDES; CARBONYLATION; CATALYSTS; KETONES; LIGANDS; ORGANOMETALLICS; PALLADIUM COMPOUNDS;

CYCLIZATION;

ACETIC ACID DERIVATIVE; AMIDE; LIGAND; ORGANOMETALLIC COMPOUND; PALLADIUM; PARGYLINE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION;

ACETATES; AMIDES; CATALYSIS; CYCLIZATION; LIGANDS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM; PARGYLINE;

EID: 79954601357     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201008139     Document Type: Article

References (76)

1. D. K. Dalvie, A. S. Kalgutkar, S. C. Khojasteh-Bakht, R. S. Obach, J. P. O'Donnell, Chem. Res. Toxicol. 2002, 15, 269
2. S. L. McGovern, E. Caselli, N. Grigorieff, B. K. Shoichet, J. Med. Chem. 2002, 45, 1712
3. M. Murcia-Soler, F. Pérez-Giménez, F. J. García-March, M. T. Salabert-Salvador, W. Díaz-Villanueva, M. J. Castro-Bleda, A. Villanueva-Pareja, J. Chem. Inf. Comput. Sci. 2004, 44, 1031
4. S. S. Shin, Y. Byun, K. M. Lim, J. K. Choi, K.-W. Lee, J. H. Moh, J. K. Kim, Y. S. Jeong, J. Y. Kim, Y. H. Choi, H.-J. Koh, Y.-H. Park, Y. I. Oh, M.-S. Noh, S. Chung, J. Med. Chem. 2004, 47, 792
5. A. Carotti, A. Carrieri, S. Chimichi, M. Boccalini, B. Cosimelli, C. Gnerre, A. Carotti, P.-A. Carrupt, B. Testa, Bioorg. Med. Chem. Lett. 2002, 12, 3551
6. S. Chimichi, M. Boccalini, B. Cosimelli, F. Dall'Acqua, G. Viola, Tetrahedron 2003, 59, 5215
7. T. Sasaki, J. Yamakoshi, M. Saito, K. Kasai, T. Matsudo, M. Kikuchi, T. Koga, K. Mori, Biosci. Biotechnol. Biochem. 1998, 62, 2145
8. R. A. Mack, W. I. Zazulak, L. A. Radov, J. E. Baer, J. D. Stewart, P. H. Elzer, C. R. Kinsolving, V. S. Georgiev, J. Med. Chem. 1988, 31, 1910.
9. H. Neumann, A. Brennführer, M. Beller, Chem. Eur. J. 2008, 14, 3645, and references therein.
10. A. Nguyen, S. Top, P. Pigeon, A. Vessires, E. A. Hillard, M.-A. Plamont, M. Huché, C. Rigamonti, G. Jaouen, Chem. Eur. J. 2009, 15, 684
11. E. Y. H. Chao, J. L. Collins, S. Gaillard, A. B. Miller, L. Wang, L. A. Orband-Miller, R. T. Nolte, D. P. McDonnell, T. M. Willson, W. J. Zuercher, Bioorg. Med. Chem. Lett. 2006, 16, 821
12. R. K. Pandey, R. D. Wakharkar, P. Kumar, Synth. Commun. 2005, 35, 2795
13. C. Olier-Reuchet, D. J. Aitken, R. Bucourt, H.-P. Husson, Tetrahedron Lett. 1995, 36, 8221
14. P. L. Coe, C. E. Scriven, J. Chem. Soc. Perkin Trans. 1 1986, 475.
15. F. Schmidt, R. T. Stemmler, J. Rudolph, C. Bolm, Chem. Soc. Rev. 2006, 35, 454
16. S. K. Das, G. Panda, V. Chaturvedi, Y. S. Manju, A. K. Gaikwad, S. Sinha, Bioorg. Med. Chem. Lett. 2007, 17, 5586
17. C. lvarez, R. lvarez, P. Corchete, J. L. López, C. Pérez-Melero, R. Peláez, M. Medarde, Bioorg. Med. Chem. 2008, 16, 5952.
18. Handbook of Organopalladium Chemistry for Organic Synthesis, Vol. II (Ed.:, E. Negishi,), Wiley, New York, 2002, p. 2309; for reviews, see
19. R. Grigg, S. P. Mutton, Tetrahedron 2010, 66, 5515
20. K. C. Majumdar, B. Chattopadhyay, P. K. Maji, S. K. Chattopadhyay, S. Samanta, Heterocycles 2010, 81, 795
21. K. C. Majumdar, P. Debnath, B. Roy, Heterocycles 2009, 78, 2661
22. I. Nakamura, Y. Yamamoto, Chem. Rev. 2004, 104, 2127
23. G. Zeni, R. C. Larock, Chem. Rev. 2004, 104, 2285
24. B. C. G. Soderberg, Coord. Chem. Rev. 2004, 248, 1085
25. S. A. Vizer, K. B. Yerzhanov, A. A. A. Al Quntar, V. M. Dembitsky, Tetrahedron 2004, 60, 5499
26. J. Muzart, Tetrahedron 2005, 61, 5955
27. N. Asao, Synlett 2006, 1645
28. S. Ma, Chem. Rev. 2005, 105, 2829; for the tandem dimerization and cyclization of acetylenic compounds, see
29. A. Jeevanandam, K. Narkunan, Y.-C. Ling, J. Org. Chem. 2001, 66, 6014
30. H. A. Wegner, S. Ahles, M. Neuburger, Chem. Eur. J. 2008, 14, 11310
31. M. G. Auzias, M. Neuburger, H. A. Wegner, Synlett 2010, 2443.
32. For reviews on palladium-catalyzed carbonylation, see
33. A. Brennführer, H. Neumann, M. Beller, ChemCatChem 2009, 1, 28
34. C. Torborg, M. Beller, Adv. Synth. Catal. 2009, 351, 3027
35. C. F. J. Barnard, Organometallics 2008, 27, 5402.
36. A. Brennführer, H. Neumann, M. Beller, Angew. Chem. 2009, 121, 4176
37. Angew. Chem. Int. Ed. 2009, 48, 4114, and references therein.
38. Recently, we reported a CCC coupling reaction of allenyl ketones without a bisoxazoline ligand. The reactivity of allenyl compounds is high enough to induce dimer formation
39. K. Kato, T. Mochida, H. Takayama, M. Kimura, H. Moriyama, A. Takeshita, Y. Kanno, Y. Inoue, H. Akita, Tetrahedron Lett. 2009, 50, 4744; for selected examples of dimerization or coupling reactions of allenyl compounds, see
40. J. A. Marshall, E. D. Robinson, J. Org. Chem. 1990, 55, 3450
41. J. A. Marshall, C. A. Sehon, J. Org. Chem. 1995, 60, 5966
42. A. S. K. Hashmi, Angew. Chem. 1995, 107, 1749
43. Angew. Chem. Int. Ed. Engl. 1995, 34, 1581
44. A. S. K. Hashmi, T. L. Ruppert, T. Knöfel, J. W. Bats, J. Org. Chem. 1997, 62, 7295
45. A. S. K. Hashmi, L. Schwarz, J.-H. Choi, T. M. Frost, Angew. Chem. 2000, 112, 2382
46. Angew. Chem. Int. Ed. 2000, 39, 2285
47. S. Ma, L. Li, Org. Lett. 2000, 2, 941
48. S. Ma, J. Zhang, L. Lu, Chem. Eur. J. 2003, 9, 2447
49. S. Ma, Z. Yu, Chem. Eur. J. 2004, 10, 2078
50. S. Ma, Z. Yu, Z. Gu, Chem. Eur. J. 2005, 11, 2351
51. Y. Deng, J. Li, S. Ma, Chem. Eur. J. 2008, 14, 4263
52. B. Alcaide, P. Almendros, T. Martínez del Campo, Eur. J. Org. Chem. 2007, 2844
53. B. Alcaide, P. Almendros, C. Aragoncillo, Chem. Eur. J. 2009, 15, 9987.
54. K. Kato, R. Teraguchi, S. Yamamura, T. Mochida, H. Akita, T. A. Peganova, N. V. Vologdin, O. V. Gusev, Synlett 2007, 638
55. K. Kato, R. Teraguchi, S. Motodate, A. Uchida, T. Mochida, T. A. Peganova, N. V. Vologdin, H. Akita, Chem. Commun. 2008, 3687
56. K. Kato, S. Motodate, T. Mochida, T. Kobayashi, H. Akita, Angew. Chem. 2009, 121, 3376
57. Angew. Chem. Int. Ed. 2009, 48, 3326
58. S. Motodate, T. Kobayashi, M. Fujii, T. Mochida, T. Kusakabe, S. Katoh, H. Akita, K. Kato, Chem. Asian J. 2010, 5, 2221
59. K. Kato, Y. Yamamoto, H. Akita, Tetrahedron Lett. 2002, 43, 6587
60. K. Kato, H. Nouchi, K. Ishikura, S. Takaishi, S. Motodate, H. Tanaka, K. Okudaira, T. Mochida, R. Nishigaki, K. Shigenobu, H. Akita, Tetrahedron 2006, 62, 2545
61. T. Kusakabe, K. Kato, S. Takaishi, S. Yamamura, T. Mochida, H. Akita, T. A. Peganova, N. V. Vologdin, O. V. Gusev, Tetrahedron 2008, 64, 319.
62. CCDC 799108 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via. See the Supporting Information.
63. P. G. Sammes, D. J. Weller, Synthesis 1995, 1205.
64. L. Duc, J. F. McGarrity, T. Meul, A. Warm, Synthesis 1992, 391.
65. For selected examples of palladium-catalyzed reactions of propargyl amides, see
66. A. Bacchi, M. Costa, N. Della Cà, B. Gabriele, G. Salerno, S. Cassoni, J. Org. Chem. 2005, 70, 4971
67. M. Costa, N. Della Cà, B. Gabriele, C. Massera, G. Salerno, M. Soliani, J. Org. Chem. 2004, 69, 2469
68. A. Arcadi, S. Cacchi, V. Carnicelli, F. Marinelli, Tetrahedron 1994, 50, 437
69. A. Lei, X. Lu, Org. Lett. 2000, 2, 2699
70. A. Arcadi, S. Cacchi, L. Cascia, G. Fabrizi, F. Marinelli, Org. Lett. 2001, 3, 2501
71. E. M. Beccalli, E. Borsini, G. Broggini, G. Palmisano, S. Sottocornola, J. Org. Chem. 2008, 73, 4746
72. E. Merkul, T. J. J. Müller, Chem. Commun. 2006, 4817
73. A. Saito, A. Matsumoto, Y. Hanzawa, Tetrahedron Lett. 2010, 51, 2247.
74. A. Bacchi, M. Costa, B. Gabriele, G. Pelizzi, G. Salerno, J. Org. Chem. 2002, 67, 4450. In this case, the carbonylation of 2a afforded maleic diester derivatives (derived from oxidative bisalkoxycarbonylation of the triple bond) in 69% yield together with oxazole 7a (14%).
75. For preliminary experiments, see the Supporting Information.
76. 2] (5 mol%) under our reaction conditions (-10°C, 24 h) afforded an unsymmetrical ketone in 18% yield together with dimeric ketones 4v (37%) and 3g (7%).