Palladium-Catalyzed decarboxylative coupling of allylic alkynoates with arynes

Organic Letters

Volumn 11, Issue 11, 2009, Pages 2309-2312

  Pi, Shao Feng ^a   Tang, Bo Xiao ^a   Li, Jin Heng ^a   Liu, Yi Lin ^a   Liang, Yun ^a  

^a HUNAN NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; ALLYL COMPOUND; BENZENE DERIVATIVE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; DECARBOXYLATION; SYNTHESIS;

ALKYNES; ALLYL COMPOUNDS; BENZENE DERIVATIVES; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; DECARBOXYLATION; MOLECULAR STRUCTURE; PALLADIUM;

EID: 66149175449     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900643r     Document Type: Article

References (52)

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. Goo-en, L. J.; Paetzold, J. Angew. Chem., Int. Ed. 2004, 43, 1095.
4. Nokami, J.; Mandai, T.; Watanabe, H.; Ohyama, H.; Tsuji, J. J. Am. Chem. Soc. 1989, 111, 4126.
5. Lou, S.; Westbrook, J. A.; Schaus, S. E. J. Am. Chem. Soc. 2004, 126, 11440.
6. Lalic, G.; Aloise, A. D.; Shair, M. D. J. Am. Chem. Soc. 2003, 125, 2852.
7. Magdziak, D.; Lalic, G.; Lee, H. M.; Fortner, K. C.; Aloise, A. D.; Shair, M. D. J. Am. Chem. Soc. 2005, 127, 7284.
8. Burger, E. C.; Tunge, J. A. Org. Lett. 2004, 6, 2603.
9. Burger, E. C.; Tunge, J. A. Org. Lett. 2004, 6, 4113.
10. Behenna, D. C.; Stoltz, B. M. J. Am. Chem. Soc. 2004, 126, 15044.
11. Trost, B. M.; Xu, J. Y. J. Am. Chem. Soc. 2005, 127, 17180.
12. Burger, E. C.; Tunge, J. A. Org. Lett. 2004, 6, 4113.
13. Kuwano, R.; Ishida, N.; Murakami, M. Chem. Commun. 2005, 3951.
14. Mohr, J. T.; Behenna, D. C.; Harned, A. M.; Stoltz, B. M. Angew. Chem., Int. Ed. 2005, 44, 6924.
15. Nakamura, M.; Hajra, L.; Endo, K.; Nakamura, E. Angew. Chem., Int. Ed. 2005, 44, 7248.
16. Trost, B. M.; Bream, R. N.; Xu, J. Angew. Chem., Int. Ed. 2006, 45, 3109.
17. McFadden, R. M.; Stoltz, B. M. J. Am. Chem. Soc. 2006, 128, 7738.
18. Marinescu, S. C.; Nishimata, T.; Mohr, J. T.; Stoltz, B. M. Org. Lett. 2008, 10, 1039.
19. Trost, B. M.; Xu, J.; Schmidt, T. J. Am. Chem. Soc. 2008, 130, 11852.
20. For selected papers on Pd-catalyzed intermolecular decarboxylative cross-coupling reactions, see: Goo-en, L. J.; Goo-en, K.; RodrI'guez, N.; Blanchot, M.; Linder, C.; Zimmermann, B. Pure Appl. Chem. 2008, 80, 1725.
21. Goo-en, L. J.; RodrI'guez, N.; Goo-en, K. Angew. Chem., Int. Ed. 2008, 47, 3100.
22. Tatamidani, H.; Yokota, K.; Kakiuchi, F.; Chatani, N. J. Org. Chem. 2004, 69, 5615.
23. Goo-en, L. J.; Deng, G.; Levy, L. M. Science 2006, 313, 662.
24. Forgione, P.; Brochu, M.-C.; St- Onge, M.; Thesen, K. H.; Bailey, M. D.; Bilodeau, F. J. Am. Chem. Soc. 2006, 128, 11350.
25. Maehara, A.; Tsurugi, H.; Satoh, T.; Miura, M. Org. Lett. 2008, 10, 1259.
26. Nakano, M.; Tsurugi, H.; Satoh, T.; Miura, M. Org. Lett. 2008, 10, 1851.
27. Wang, C.; Tunge, J. A. J. Am. Chem. Soc. 2008, 130, 8118.
28. Becht, J.-M.; Drian, C. L. Org. Lett. 2008, 10, 3161.
29. Shintani, R.; Park, S.; Shirozu, F.; Murakami, M.; Hayashi, T. J. Am. Chem. Soc. 2008, 130, 16174.
30. Shang, R.; Fu, Y.; Li, J.-B.; Zhang, S.- L.; Guo, Q.-X.; Liu, L. J. Am. Chem. Soc. 2009, 131, 5738-5739.
31. 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.
32. Wang, C.; Tunge, J. A. Org. Lett. 2005, 7, 2137.
33. Burger, E. C.; Tunge, J. A. J. Am. Chem. Soc. 2006, 128, 10002.
34. Waetzig, S. R.; Rayabarapu, D. K.; Weaver, J. D.; Tunge, J. A. Angew. Chem., Int. Ed. 2006, 45, 4977.
35. Waetzig, S. R.; Tunge, J. A. J. Am. Chem. Soc. 2007, 129, 4138.
36. Waetzig, S. R.; Tunge, J. A. J. Am. Chem. Soc. 2007, 129, 14860.
37. Yeagley, A. A.; Chruma, J. J. Org. Lett. 2007, 9, 2879.
38. Weaver, J. D.; Tunge, J. A. Org. Lett. 2008, 10, 4657.
39. Fields, W. H.; Khan, A. K.; Sabat, M.; Chruma, J. J. Org. Lett. 2008, 10, 5131.
40. Sim, S. H.; Park, H.-J.; Lee, S. I.; Chung, Y. K. Org. Lett. 2008, 10, 433.
41. Huang, X.-C.; Wang, F.; Liang, Y.; Li, J.-H. Org. Lett. 2009, 11, 1139.
42. For selected papers, see: Fürstner, A.; Davies, P. W. Angew. Chem., Int. Ed. 2007, 46, 3410.
43. Fairamb, I. J. S. Angew. Chem., Int. Ed. 2004, 43, 1048.
44. Brown, S.; Clarkson, S.; Grigg, R.; Sridharan, V. Tetrahedron Lett. 1993, 34, 157.
45. For selected reviews, see: Kessar, S. V. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, p 483.
46. Peña, D.; Pe'rez, D.; Guitia'n, E. Angew. Chem., Int. Ed. 2006, 45, 3579.
47. Pellissier, H.; Santelli, M. Tetrahedron 2003, 59, 701.
48. For papers on capturing the Pd-π-allyl intermediates, which is generated from the reaction of Pd, allyls, and alkynes, to synthesize 1-allyl- 2-ethynylbenzenes by a three-component coupling process including arynes, see: Jeganmohn, M.; Chen, C.-H. Org. Lett. 2004, 6, 2821.
49. Xie, C.; Liu, L.; Zhang, Y.; Xu, P. Org. Lett. 2008, 10, 2393.
50. Bhuvaneswari, S.; Jeganmohan, M.; Yang, M. C.; Cheng, C. H. Chem. Commun. 2008, 2158.
51. Jeganmohan, M.; Bhuvaneswari, S.; Cheng, C.-H. Angew. Chem., Int. Ed. 2009, 48, 391.
52. 1H NMR and C-H COSY (HSQC and HMBC) spectra of the product 5 (see Supporting Information).