Palladacycle-catalyzed deacetonative sonogashira coupling of aryl propargyl alcohols with aryl chlorides

Journal of Organic Chemistry

Volumn 78, Issue 20, 2013, Pages 10506-10511

  Hu, Hao ^a   Yang, Fan ^a   Wu, Yangjie ^a  

^a ZHENGZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL CHLORIDE; CATALYST SYSTEM; ELECTRON-RICH; PALLADACYCLES; PROPARGYL ALCOHOL; SONOGASHIRA COUPLING;

CHEMICAL REACTIONS;

CHLORINE COMPOUNDS;

ALCOHOL DERIVATIVE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; DEACETONATIVE SONOGASHIRA COUPLING; QUANTUM YIELD; REACTION ANALYSIS; SONOGASHIRA REACTION; STEREOSPECIFICITY;

EID: 84886427050     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo4014657     Document Type: Article

References (47)

1. Sonogashira, K. J. Organomet. Chem. 2002, 653, 46
2. Negishi, E.; Anastasia, L. Chem. Rev. 2003, 103, 1979
3. Tykwinski, R. R. Angew. Chem., Int. Ed. 2003, 42, 1566
4. Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4442
5. Chinchilla, R.; Nájera, C. Chem. Rev. 2007, 107, 874
6. Doucet, H.; Hierso, J.-C. Angew. Chem., Int. Ed. 2007, 46, 834
7. Plenio, H. Angew. Chem., Int. Ed. 2008, 47, 6954
8. Chinchilla, R.; Nájera, C. Chem. Soc. Rev. 2011, 40, 5084
9. Eberhard, M. R.; Wang, Z.; Jensen, C. M. Chem. Commun. 2002, 818
10. Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176
11. Choudary, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2002, 124, 14127
12. Gelman, D.; Buchwald, S. L. Angew. Chem., Int. Ed. 2003, 42, 5993
13. Kollhofer, A.; Pullmann, T.; Plenio, H. Angew. Chem., Int. Ed. 2003, 42, 1056
14. Komáromi, A.; Novák, Z. Chem. Commun. 2008, 4968
15. Anderson, K. W.; Buchwald, S. L. Angew. Chem., Int. Ed. 2005, 44, 6173
16. Park, J.; Park, E.; Kim, A.; Park, S.-A.; Lee, Y.; Chi, K. W.; Jung, Y. H.; Kim, I. S. J. Org. Chem. 2011, 76, 2214
17. Kim, Y.; Park, A.; Park, K.; Lee, S. Tetrahedron Lett. 2011, 52, 1766
18. Moon, J.; Jeong, M.; Nam, H.; Ju, J.; Moon, J. H.; Jung, H. M.; Lee, S. Org. Lett. 2008, 10, 945
19. Moon, J.; Jang, M.; Lee, S. J. Org. Chem. 2009, 74, 1403
20. Kim, H.; Lee, P. H. Adv. Synth. Catal. 2009, 351, 2827
21. Zhao, D.-B.; Gao, C.; Su, X.-Y.; He, Y.-Q.; You, J.-S.; Xue, Y. Chem. Commun. 2010, 46, 9049
22. Li, T.-Y.; Qu, X.-M.; Zhu, Y.; Sun, P.; Yang, H.-L.; Shan, Y.-Q.; Zhang, H.-X.; Liu, D.-F.; Zhang, X.; Mao, J.-C. Adv. Synth. Catal. 2011, 353, 2731
23. Reddy, P. V.; Srinivas, P.; Annapurna, M.; Bhargava, S.; Wagler, J.; Mirzadeh, N.; Kantam, M. L. Adv. Synth. Catal. 2013, 355, 705
24. Chow, H.-F.; Wan, C.-W.; Low, K.-H.; Yeung, Y.-Y. J. Org. Chem. 2001, 66, 1910
25. Novák, Z.; Nemes, P.; Kotschy, A. Org. Lett. 2004, 6, 4917
26. Shirakawa, E.; Kitabata, T.; Otsuka, H.; Tsuchimoto, T. Tetrahedron 2005, 61, 9878
27. Yi, C. Y.; Hua, R. M.; Zeng, H. X.; Huang, Q. F. Adv. Synth. Catal. 2007, 349, 1738
28. Csékei, M.; Novák, Z.; Kotschy, A. Tetrahedron 2008, 64, 975
29. Hung, T.-T.; Huang, C.-M.; Tsai, F.-Y. ChemCatChem 2012, 4, 540
30. Huo, S.-Q.; Wu, Y.-J.; Du, C.-X.; Zhu, Y.; Yuan, H.-Z.; Mao, X.-A. J. Organomet. Chem. 1994, 483, 139
31. Yang, F.; Cui, X.-L.; Li, Y.-N.; Zhang, J.-L.; Ren, G.-R.; Wu, Y.-J. Tetrahedron 2007, 63, 1963
32. Yang, F.; Wu, Y.-J. Eur. J. Org. Chem. 2007, 3476
33. Ren, G.-R.; Cui, X.-L.; Yang, E.-B.; Yang, F.; Wu, Y.-J. Tetrahedron 2010, 66, 4022
34. Xu, K.; Yang, F.; Zhang, G.-D.; Wu, Y.-J. Green Chem. 2013, 15, 1055
35. Xu, K.; Hu, H.; Yang, F.; Wu, Y.-J. Eur. J. Org. Chem. 2013, 319
36. Li, X.; Yang, F.; Wu, Y.-J. J. Org. Chem. 2013, 78, 4543
37. Park, K.; Bae, G.; Moon, J.; Choe, J.; Song, K. H.; Lee, S. J. Org. Chem. 2010, 75, 6244
38. Wan, S.; Wang, S. R.; Lu, W. J. J. Org. Chem. 2006, 71, 4349
39. Castagnolo, D.; Botta, M. Eur. J. Org. Chem. 2010, 3224
40. Rao, M. L. N.; Jadhav, D. N.; Dasgupta, P. Org. Lett. 2010, 12, 2048
41. Yamane, Y.; Liu, X. H.; Hamasaki, A.; Ishida, T.; Haruta, M.; Yokoyama, T.; Tokunaga, M. Org. Lett. 2009, 11, 5162
42. Truong, T.; Daugulis, O. Org. Lett. 2011, 13, 4172
43. D'Auria, M.; Piancatelli, G.; Ferri, T. J. Org. Chem. 1990, 55, 4019
44. Iaroshenko, V. O.; Ali, S.; Babar, T. M.; Abbasi, M. S. A.; Sosnovskikh, V. Y.; Villinger, A.; Tolmachev, A.; Langer, P. Tetrahedron 2013, 69, 3167
45. Maji, M. S.; Murarka, S.; Studer, A. Org. Lett. 2010, 12, 3878
46. Liang, B.; Dai, M. J.; Chen, J. H.; Yang, Z. J. Org. Chem. 2005, 70, 391
47. Shi, Y. L.; Roth, K. E.; Ramgren, S. D.; Blum, S. A. J. Am. Chem. Soc. 2009, 131, 18022