Palladium-catalyzed decarboxylative coupling of alkynyl carboxylic acids with benzyl halides or aryl halides

Journal of Organic Chemistry

Volumn 75, Issue 15, 2010, Pages 5259-5264

  Zhang, Wen Wu ^a   Zhang, Xing Guo ^a   Li, Jin Heng ^a,b  

^a WENZHOU UNIVERSITY   (China)

^b HUNAN NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNYLS; ARYL CHLORIDE; ARYL HALIDES; BENZYL CHLORIDES; BENZYL HALIDES; COUPLING REACTION; DIARYLALKYNES; GOOD YIELD; OPTIMAL CONDITIONS;

ACETYLENE; CHLORINE COMPOUNDS; METAL HALIDES; ORGANIC ACIDS; PALLADIUM; SYNTHESIS (CHEMICAL);

CARBOXYLIC ACIDS;

BENZYL DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; HALIDE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; DECARBOXYLATION; SYNTHESIS;

CARBOXYLIC ACIDS; CATALYSIS; HALOGENS; MAGNETIC RESONANCE SPECTROSCOPY; PALLADIUM; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 77955142798     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1010284     Document Type: Article

References (69)

1. Myers, A. G.; Tanaka, D.; Mannion, M. R. J. Am. Chem. Soc. 2002, 124, 11250
2. Tanaka, D.; Myers, A. G. Org. Lett. 2004, 6, 433
3. Gooen, L. J.; Paetzold, J. Angew. Chem., Int. Ed. 2004, 43, 1095
4. Zhang, S.-L.; Fu, Y.; Shang, R.; Guo, Q.-X.; Liu, L. J. Am. Chem. Soc. 2010, 132, 638
5. Nokami, J.; Mandai, T.; Watanabe, H.; Ohyama, H.; Tsuji, J. J. Am. Chem. Soc. 1989, 111, 4126
6. Lou, S.; Westbrook, J. A.; Schaus, S. E. J. Am. Chem. Soc. 2004, 126, 11440
7. Lalic, G.; Aloise, A. D.; Shair, M. D. J. Am. Chem. Soc. 2003, 125, 2852
8. Magdziak, D.; Lalic, G.; Lee, H. M.; Fortner, K. C.; Aloise, A. D.; Shair, M. D. J. Am. Chem. Soc. 2005, 127, 7284
9. Burger, E. C.; Tunge, J. A. Org. Lett. 2004, 6, 2603
10. Burger, E. C.; Tunge, J. A. Org. Lett. 2004, 6, 4113
11. Behenna, D. C.; Stoltz, B. M. J. Am. Chem. Soc. 2004, 126, 15044
12. Trost, B. M.; Xu, J. Y. J. Am. Chem. Soc. 2005, 127, 17180
13. Burger, E. C.; Tunge, J. A. Org. Lett. 2004, 6, 4113
14. Kuwano, R.; Ishida, N.; Murakami, M. Chem. Commun. 2005, 3951
15. Mohr, J. T.; Behenna, D. C.; Harned, A. M.; Stoltz, B. M. Angew. Chem., Int. Ed. 2005, 44, 6924
16. Nakamura, M.; Hajra, L.; Endo, K.; Nakamura, E. Angew. Chem., Int. Ed. 2005, 44, 7248
17. Trost, B. M.; Bream, R. N.; Xu, J. Angew. Chem., Int. Ed. 2006, 45, 3109
18. McFadden, R. M.; Stoltz, B. M. J. Am. Chem. Soc. 2006, 128, 7738
19. Marinescu, S. C.; Nishimata, T.; Mohr, J. T.; Stoltz, B. M. Org. Lett. 2008, 10, 1039
20. Trost, B. M.; Xu, J.; Schmidt, T. J. Am. Chem. Soc. 2008, 130, 11852
21. For selected papers on Pd-catalyzed intermolecular decarboxylative cross-coupling reactions, see: Goossen, L. J.; Goossen, K.; Rodríguez, N.; Blanchot, M.; Linder, C.; Zimmermann, B. Pure Appl. Chem. 2008, 80, 1725
22. Goossen, L. J.; Rodríguez, N.; Goossen, K. Angew. Chem., Int. Ed. 2008, 47, 3100
23. Tatamidani, H.; Yokota, K.; Kakiuchi, F.; Chatani, N. J. Org. Chem. 2004, 69, 5615
24. Gooen, L. J.; Deng, G.; Levy, L. M. Science 2006, 313, 662
25. Forgione, P.; Brochu, M.-C.; St-Onge, M.; Thesen, K. H.; Bailey, M. D.; Bilodeau, F. J. Am. Chem. Soc. 2006, 128, 11350
26. Maehara, A.; Tsurugi, H.; Satoh, T.; Miura, M. Org. Lett. 2008, 10, 1259
27. Nakano, M.; Tsurugi, H.; Satoh, T.; Miura, M. Org. Lett. 2008, 10, 1851
28. Wang, C.; Tunge, J. A. J. Am. Chem. Soc. 2008, 130, 8118
29. Becht, J.-M.; Drian, C. L. Org. Lett. 2008, 10, 3161
30. Shintani, R.; Park, S.; Shirozu, F.; Murakami, M.; Hayashi, T. J. Am. Chem. Soc. 2008, 130, 16174
31. Shang, R.; Fu, Y.; Li, J.-B.; Zhang, S.-L.; Guo, Q.-X.; Liu, L. J. Am. Chem. Soc. 2009, 131, 5738
32. Miyasaki, M.; Fukushima, A.; Satoh, T.; Hirano, K.; Miura, M. Chem.- Eur. J. 2009, 15, 3674
33. Xie, K.; Yang, Z.; Zhou, X.; Li, X.; Wang, S.; Tan, Z.; An, X.; Guo, C.-C. Org. Lett. 2010, 12, 1564
34. Bilodeau, F.; Brochu, M.-C.; Guimond, N.; Thesen, K. H.; Forgione, P. J. Org. Chem. 2010, 75, 1550
35. Gooen, L. J.; Rodriguez, N.; Lange, P. P.; Linder, C. Angew. Chem., Int. Ed. 2010, 49, 1111
36. Yamashita, M.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2010, 12, 592
37. For selected papers on Pd-catalyzed intramolecular decarboxylative cross-coupling reactions, see: Rayabarapu, D. K.; Tunge, J. A. J. Am. Chem. Soc. 2005, 127, 13510
38. Wang, C.; Tunge, J. A. Org. Lett. 2005, 7, 2137
39. Burger, E. C.; Tunge, J. A. J. Am. Chem. Soc. 2006, 128, 10002
40. Waetzig, S. R.; Rayabarapu, D. K.; Weaver, J. D.; Tunge, J. A. Angew. Chem., Int. Ed. 2006, 45, 4977
41. Waetzig, S. R.; Tunge, J. A. J. Am. Chem. Soc. 2007, 129, 4138
42. Waetzig, S. R.; Tunge, J. A. J. Am. Chem. Soc. 2007, 129, 14860
43. Yeagley, A. A.; Chruma, J. J. Org. Lett. 2007, 9, 2879
44. Weaver, J. D.; Tunge, J. A. Org. Lett. 2008, 10, 4657
45. Fields, W. H.; Khan, A. K.; Sabat, M.; Chruma, J. J. Org. Lett. 2008, 10, 5131
46. Sim, S. H.; Park, H.-J.; Lee, S. I.; Chung, Y. K. Org. Lett. 2008, 10, 433
47. Huang, X.-C.; Wang, F.; Liang, Y.; Li, J.-H. Org. Lett. 2009, 11, 1139
48. Moon, J.; Jeong, M.; Nam, H.; Ju, J.; Moon, J. H.; Jung, H. M.; Lee, S. Org. Lett. 2008, 10, 945
49. Moon, J.; Jang, M.; Lee, S. J. Org. Chem. 2009, 74, 1403
50. Kim, H.; Lee, P. H. Adv. Synth. Catal. 2009, 351, 2827
51. For papers on Cu-catalyzed decarboxylation of 2-alkynoic acids, see: Kolarovič, A.; Fáberová, Z. J. Org. Chem. 2009, 74, 7199
52. Jia, W.; Jiao, N. Org. Lett. 2010, 12, 2000
53. Yu, M.; Pan, D.; Jia, W.; Chen, W.; Jiao, N. Tetrahedron Lett. 2010, 51, 1287
54. Pi, S.-F.; Tang, B.-X.; Li, J.-H.; Liu, Y.-L.; Liang, Y. Org. Lett. 2009, 11, 2309
55. For selected reviews on the Sonogashira cross-coupling reaction, see: Sonogashira, K. J. Organomet. Chem. 2002, 653, 46
56. Negishi, E.-i.; Anastasia, L. Chem. Rev. 2003, 103, 1979
57. Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4442
58. Chinchilla, R.; Nájera, C. Chem. Rev. 2007, 107, 874
59. Li, C.; Li, W.; Wang, J. Tetrahedron Lett. 2009, 50, 2533
60. Adjabeng, G.; Brenstrum, T.; Frampton, C. S.; Robertson, A. J.; Hillhous, J.; McNulty, J.; Capretta, A. J. Org. Chem. 2004, 69, 5082
61. Li, C.; Wang, J. J. Org. Chem. 2007, 72, 7431
62. Oku, M.; Arai, S.; Katayama, K.; Shioiri, T. Synlett 2000, 493
63. Bieber, L. W.; da Silva, M. F. Tetrahedron Lett. 2007, 48, 7088
64. Bushby, R. J.; Ferber, G. J. J. Chem. Soc., Chem. Commun. 1973, 407
65. Huang, Q.; Hua, R. Chem.- Eur. J. 2007, 13, 8333
66. Lunazzi, L.; Mangini, A.; Placucci, G.; Spagnolo, P.; Tiecco, M. J. Chem. Soc., Perkin Trans. 2 1972, 192
67. Ding, Q.; Wu, J. Adv. Synth. Catal. 2008, 350, 1850
68. Yu, X.; Wu, J. J. Comb. Chem. 2010, 12, 238
69. Liang, Y.; Xie, Y.-X.; Li, J.-H. Synthesis 2007, 400