Efficient synthesis of benzothiophenes by an unusual palladiumcatalyzed vinylic C-S coupling

Angewandte Chemie - International Edition

Volumn 48, Issue 38, 2009, Pages 7064-7068

  Bryan, Christopher S ^a   Braunger, Julia A ^a   Lautens, Mark ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

Cross coupling; Palladium; Sulfur heterocycles; Synthetic methods; Tandem catalysis

Indexed keywords

ALKENYL; C-C BONDS; CATALYTIC CONDITIONS; CATALYTIC PROCESS; CROSS-COUPLING; EFFICIENT SYNTHESIS; FUNCTIONALIZED; ORGANOBORON; SONOGASHIRA COUPLING; SULFUR HETEROCYCLES; SYNTHETIC METHODS; TANDEM CATALYSIS; THIOPHENOLS;

ACETYLENE; OLEFINS; PALLADIUM; SULFUR; THIOPHENE;

CATALYSIS;

BENZOTHIOPHENE; PALLADIUM; SULFUR DERIVATIVE; THIOPHENE DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

CATALYSIS; MODELS, MOLECULAR; PALLADIUM; SULFUR COMPOUNDS; THIOPHENES; VINYL COMPOUNDS;

EID: 70349898232     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200902843     Document Type: Article

References (91)

1. Handbook of Organopalladium Chemistry for Organic Synthesis, Vol.1 (Ed.: E-i. Negishi), Wiley-Interscience, New York, 2002.
2. For reviews on metal-catalyzed cross-coupling reactions, see: a) J. F. Hartwig, Nature 2008, 455, 314;
3. b) G Fu, Ace. Chem. Res. 2008, 41, 1555;
4. c) K. C Nicolaou, P. G Bulger, D Sarlah, Angew. Chem. 2005, 117, 4516;
5. Angew. Chem. Int. Ed. 2005, 44, 4442;
6. d) Metal-Catalyzed Cross-Coupling Reactions, 2nd ed. (Eds.: A. de Meijere, F. Diederich), Wiley-VCH, Weinheim, 2004.
7. For reviews on catalytic amination, see : a) J. F. Hartwig, Acc. Chem. Res. 2008, 41, 1534;
8. b) D S. Surry, S. L. Buchwald, Angew. Chem. 2008, 120, 6438;
9. Angew. Chem. Int. Ed. 2008, 47, 6338;
10. c) J Barluenga, C Valdês, Chem. Commun. 2006, 4891;
11. d) S. V Ley, A. Thomas, Angew. Chem. 2003, 115, 5558;
12. Angew. Chem. Int. Ed. 2003, 42, 5400;
13. Corrigendum: S. V Ley, A. Thomas, Angew. Chem. 2004,116,1061;
14. Angew. Chem. Int. Ed. 2004, 43, 1043.
15. For catalytic etherification, see: a) C H. Burgos, T E. Barder, X. Huang, S. L. Buchwald, Angew. Chem. 2006, 118, 4427;
16. Angew. Chem. Int. Ed. 2006, 45, 4321;
17. b) A. V Vorogushin, X. Huang, S. L. Buchwald, J. Am. Chem. Soc. 2005, 127, 8146;
18. c) K. E. Torraca, X. Huang, C A. Parrish, S. L. Buchwald, J. Am. Chem. Soc. 2001, 123, 10770;
19. d) Q. Shelby, N Kataoka, G. Mann, I F. Hartwig, J. Am. Chem. Soc. 2000, 122, 10718;
20. e) R. A. Altman, A. Shafir, A. Choi, P. A. Lichtor, S. L. Buchwald, J. Org. Chem. 2008, 73, 284;
21. f) R. Gujadhur, C. G. Bates, D Venkataraman, Org. Lett. 2001, 3, 4315.
22. Sulfur-containing compounds display strong coordinating and adsorptive properties; see: a) E. Alvaro, J. F. Hartwig, J. Am. Chem. Soc. 2009, 131, 7858;
23. b) G Mann, D Barañano, J. F. Hartwig, A. L. Rheingold, I. A. Guzei, J. Am. Chem. Soc. 1998, 120, 9205;
24. c) J. Louie, J. F. Hartwig, J. Am. Chem. Soc. 1995, 117, 11598;
25. d) L. L. Hegedus, R. W McCabe in Catalyst Poisoning, Marcel Dekker, New York, 1984;
26. e) A. T Hutton in Comprehensive Coordination Chemistry, Vol.5 (Eds. : G Wilkinson, R. D Gillard, J. A. McCleverty), Pergamon, Oxford, 1984, p. 1131.
27. During the course of this study, an excellent publication describing the use of Zn salts to prevent catalyst poisoning in a palladium-catalyzed C-S coupling reaction appeared: C. C. Eichman, I P. Stambuli, J. Org. Chem. 2009, 74, 4005.
28. For reviews on metal-catalyzed C-S bond formation, see : a) I. P. Beletskaya, V P. Ananikov, Eur. J Org. Chem. 2007, 3431;
29. b) T Kondo, T.-a. Mitsudo, Chem. Rev. 2000, 100, 3205.
30. a) J.-Y. Lee, P. H. Lee, J. Org. Chem. 2008, 73, 7413;
31. b) M. A. Fernández-Rodriguez, Q. Shen, J. F. Hartwig, J. Am. Chem. Soc. 2006, 128, 2180;
32. c) C Mispelaere-Canivet, J. F. Spindler, S. Perrio, P. Beslin, Tetrahedron 2005, 61, 5253;
33. d) M. Murata, S. L. Buchwald, Tetrahedron 2004, 60, 7397;
34. e) T. Itoh, T Mase, Org. Lett. 2004, 6, 4587;
35. f) G. Y Li, Angew. Chem. 2001, 113, 1561;
36. Angew. Chem. Int. Ed. 2001, 40, 1513;
37. g) U Schopfer, A. Schlapbach, Tetrahedron 2001, 57, 3069;
38. h) N Zheng, J. C. McWilliams, F. J. Fleitz, I D Armstrong J.II, R. P. Volante, J. Org. Chem. 1998, 63, 9606;
39. i) T Migita, T Shimizu, Y Asami, J.-i. Shiobara, Y Kato, M. Kosugi, Bull. Chem. Soc. Jpn. 1980, 53, 1385;
40. j) M. Kosugi, T Shimizu, T Migita, Chem. Lett. 1978, 13.
41. a) D Ma, S. Xie, P. Xue, X. Zhang, J. Dong, Y Jiang, Angew. Chem. 2009, 121, 4289;
42. Angew. Chem. Int. Ed. 2009, 48, 4222;
43. b) M. Carril, R. SanMartin, E. Domínguez, I. Tellitu, Chem. Eur. J. 2007, 13, 5100;
44. c) A. K. Verma, J. Singh, R. Chaudhary, Tetrahedron Lett. 2007, 48, 7199;
45. d) X. Lv, W Bao, J. Org. Chem. 2007, 72, 3863;
46. e) C G Bates, R. K. Gujadhur, D. Venkataraman, Org. Lett. 2002, 4, 2803.
47. a) Y Zhang, K. C Ngeow, J. Y Ying, Org. Lett. 2007, 9, 3495;
48. b) H. J. Cristau, B. Chabaud, A. Chene, H. Christol, Synthesis 1981, 892.
49. Y.-C. Wong, T T. Jayanth, C-H. Cheng, Org. Lett. 2006, 8, 5613.
50. A. Correa, M. Carril, C Bolm, Angew. Chem. 2008, 120, 2922;
51. Angew. Chem. Int. Ed. 2008, 47, 2880.
52. V P. Reddy, A. V Kumar, K. Swapna, K. R. Rao, Org. Lett. 2009, 11, 1697.
53. For examples of intermolecular copper-catalyzed C-S coupling reactions of vinyl halides, see : a) M. S. Kabir, M. L. Van Linn, A. Monte, I M. Cook, Org. Lett. 2008, 10, 3363;
54. b) B. Jiang, H. Tian, A.-G. Huang, M. Xu, Org. Lett. 2008, 10, 2737;
55. c) Y Zheng, X. Du, W Bao, Tetrahedron Lett. 2006, 47,1217;
56. d) C G Bates, P. Saejueng, M. Q. Doherty, D Venkataraman, Org. Lett. 2004, 6, 5005.
57. For an intramolecular copper-catalyzed S-vinylation, see: Q. Zhao, L. Li, Y Fang, D Sun, C Li, J. Org. Chem. 2009, 74, 459.
58. For examples of intermolecular palladium-catalyzed S-vinylation, see: a) X. Moreau, J.-M. Campagne, J. Organomet. Chem. 2003, 687, 322;
59. b) I. G. Trostyanskaya, D. Y. Titskiy, E. A. Anufrieva, A. A. Borisenko, M. A. Kazankova, I. P. Beletskaya, Russ. Chem. Bull. 2001, 50, 2095;
60. c) A. M. Rane, E. I. Miranda, J. A. Soderquist, Tetrahedron Lett. 1994, 35, 3225;
61. d) S.-I. Murahashi, M. Yamamura, K.-i. Yanagisawa, N Mita, K. Kondo, J. Org. Chem. 1979, 44, 2408.
62. a) L.-F. Tietze, G. Brasche, K. Gericke, Domino Reactions in Organic Synthesis, Wiley-VCH, Weinheim, 2006;
63. b) D. E. Fogg, E. S. dos Santos, Coord. Chem. Rev. 2004, 248, 2365.
64. Z. Qin, I. Kasrati, E. P. Chandrasena, H. Liu, P. Yao, P. A. Petukhov, I L. Bolton, G R. I Thatcher, J. Med. Chem. 2007, 50, 2682.
65. C-N Hsiao, T Kolasa, Tetrahedron Lett. 1992, 33, 2629.
66. For catalytic approaches to benzothiophenes, see: a) K. Inamoto, Y Arai, K. Hiroya, T. Doi, Chem. Commun. 2008, 5529;
67. b) I. Nakamura, T Sato, Y Yamamoto, Angew. Chem. 2006, 118, 4585;
68. Angew. Chem. Int. Ed. 2006, 45, 4473;
69. c) M. C Willis, D. Taylor, A. T Gillmore, Tetrahedron 2006, 62, 11513.
70. C Bryan, V Aurregi, M. Lautens, Org. Synth. 2009, 86, 36.
71. a) Y-Q. Fang, M. Lautens, J. Org. Chem. 2008, 73, 538;
72. b) Y-Q. Fang, M. Lautens, Org. Lett. 2005, 7, 3549;
73. c) Y-Q. Fang, I Yuen, M. Lautens, J. Org. Chem. 2007, 72, 5152;
74. d)Y-Q. Fang, R. Karisch, M. Lautens, J. Org. Chem. 2007, 72, 1341;
75. e) S. Thielges, E. Meddah, P. Bisseret, I Eustache, Tetrahedron Lett. 2004, 45, 907.
76. A. Fayol, Y-Q. Fang, M. Lautens, Org. Lett. 2006, 8, 4203.
77. M. Nagamochi, Y-Q. Fang, M. Lautens, Org. Lett. 2007, 9, 2955.
78. J. Yuen, Y-Q. Fang, M. Lautens, Org. Lett. 2006, 8, 653-656.
79. a) C. S. Bryan, M. Lautens, Org. Lett. 2008, 10, 4633; for an example of direct arylation paired with Suzuki-Miyaura coupling, see:
80. b) D. Chai, M. Lautens, J. Org. Chem. 2009, 74, 3054.
81. T. O. Vieria, L. A. Meaney, Y-L. Shi, H. Alper, Org. Lett. 2008, 10, 4899.
82. The starting materials, such as la, can be prepared readily from the corresponding 2-halobenzaldehydes; see the Supporting Information for details.
83. T. E. Barder, S. D. Walker, J. R. Martinelli, S. L. Buchwald, J. Am. Chem. Soc. 2005, 127, 4685.
84. For the cross-coupling of trifluoroborates, see : a) G. A. Molander, D. L. Sandrock, J. Am. Chem. Soc. 2008, 130, 15792;
85. b) Y. Bolshan, R. A. Batey, Angew. Chem. 2008, 120, 2139;
86. Angew. Chem. Int. Ed. 2008, 47, 2109;
87. c) S. Darses, J.-P. Genêt, J.-L. Brayer, J.-P. Demoute, Tetrahedron Lett. 1997, 38, 4393.
88. For N-heterocycle synthesis through the palladium-catalyzed intramolecular addition of a nitrogen nucleophile to an alkyne, see: a) L. Kaspar, L. Ackermann, Tetrahedron Lett. 2005, 61, 11311;
89. b) S. Cacchi, V. Carnicelli, F. Marinelli, J. Organomet. Chem. 1994, 475, 289;
90. c) K. Utimoto, H. Miwa, H. Nozaki, Tetrahedron Lett. 1981, 22, 4277.
91. T Jeffery, Tetrahedron 1996, 52, 10113-10130.