Pd(0)-catalyzed decarboxylative coupling and tandem C-H arylation/decarboxylation for the synthesis of heteroaromatic biaryls

Journal of Organic Chemistry

Volumn 77, Issue 20, 2012, Pages 9384-9390

  Nandi, Debkumar ^a   Jhou, Yang Ming ^a   Lee, Jhen Yi ^a   Kuo, Bing Chiuan ^a   Liu, Chien Yu ^a   Huang, Pei Wen ^a   Lee, Hon Man ^a  

^a NATIONAL CHANGHUA UNIVERSITY OF EDUCATION   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL HALIDES; BIARYLS; C-H ARYLATION; CARBENE COMPLEXES; ISOXAZOLES;

CARBOXYLATION; CARBOXYLIC ACIDS;

PALLADIUM COMPOUNDS;

IMIDAZO[1,2 A]PYRIDINE DERIVATIVE; ISOXAZOLE; PALLADIUM;

ARTICLE; ARYLATION; CATALYSIS; DECARBOXYLATION; DRUG STRUCTURE; DRUG SYNTHESIS;

CATALYSIS; DECARBOXYLATION; HYDROCARBONS, AROMATIC; MOLECULAR STRUCTURE; PALLADIUM;

EID: 84867733060     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo3015837     Document Type: Article

References (40)

1. Garg, N. K.; Sarpong, R.; Stoltz, B. M. J. Am. Chem. Soc. 2002, 124, 13179
2. Cacchi, S.; Fabrizi, G. Chem. Rev. 2005, 105, 2873
3. Godula, K.; Sames, D. Science 2006, 312, 67
4. Campeau, L.-C.; Fagnou, K. Chem. Commun. 2006, 1253
5. Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174
6. McGlacken, G. P.; Bateman, L. M. Chem. Soc. Rev. 2009, 38, 2447
7. Baudoin, O. Angew. Chem., Int. Ed. 2007, 46, 1373
8. Rodriguez, N.; Goossen, L. J. Chem. Soc. Rev. 2011, 40, 5030
9. Cornella, J.; Larrosa, I. Synthesis 2012, 44, 653
10. Seregin, I. V.; Gevorgyan, V. Chem. Soc. Rev. 2007, 36, 1173
11. Ackermann, L.; Vicente, R.; Kapdi, A. R. Angew. Chem., Int. Ed. 2009, 48, 9792
12. Roger, J.; Gottumukkala, A. L.; Doucet, H. ChemCatChem 2010, 2, 20
13. Schnürch, M.; Flasik, R.; Khan, A. F.; Spina, M.; Mihovilovic, M. D.; Stanetty, P. Eur. J. Org. Chem. 2006, 2006, 3283
14. Forgione, P.; Brochu, M.-C.; St-Onge, M.; Thesen, K. H.; Bailey, M. D.; Bilodeau, F. J. Am. Chem. Soc. 2006, 128, 11350
15. Miyasaka, M.; Fukushima, A.; Satoh, T.; Hirano, K.; Miura, M. Chem.-Eur. J. 2009, 15, 3674
16. Bilodeau, F.; Brochu, M.-C.; Guimond, N.; Thesen, K. H.; Forgione, P. J. Org. Chem. 2010, 75, 1550
17. Shang, R.; Xu, Q.; Jiang, Y.-Y.; Wang, Y.; Liu, L. Org. Lett. 2010, 12, 1000
18. Goossen, L. J.; Rodríguez, N.; Melzer, B.; Linder, C.; Deng, G.; Levy, L. M. J. Am. Chem. Soc. 2007, 129, 4824
19. Gooßen, L. J.; Rodríguez, N.; Lange, P. P.; Linder, C. Angew. Chem., Int. Ed. 2010, 49, 1111
20. Zhang, F.; Greaney, M. F. Org. Lett. 2010, 12, 4745
21. Gooßen, L. J.; Lange, P. P.; Rodríguez, N.; Linder, C. Chem.-Eur. J. 2010, 16, 3906
22. Shang, R.; Fu, Y.; Wang, Y.; Xu, Q.; Yu, H.-Z.; Liu, L. Angew. Chem., Int. Ed. 2009, 48, 9350
23. Arroyave, F. A.; Reynolds, J. R. Org. Lett. 2010, 12, 1328
24. Lee, J.-Y.; Cheng, P.-Y.; Tsai, Y.-H.; Lin, G.-R.; Liu, S.-P.; Sie, M.-H.; Lee, H. M. Organometallics 2010, 29, 3901
25. Fu, H. Y.; Chen, L.; Doucet, H. J. Org. Chem. 2012, 77, 4473
26. Kumar, P. V.; Lin, W.-S.; Shen, J.-S.; Nandi, D.; Lee, H. M. Organometallics 2011, 30, 5160
27. Becht, J.-M.; Catala, C.; Le Drian, C.; Wagner, A. Org. Lett. 2007, 9, 1781
28. Cavell, K. J.; Stufkens, D. J.; Vrieze, K. Inorg. Chim. Acta 1981, 47, 67
29. Lombardino, J. G. J. Org. Chem. 1965, 30, 2403
30. Xu, W. M.; Tang, E.; Huang, X. Tetrahedron 2005, 61, 501
31. Kamata, K.; Kasai, J.; Yamaguchi, K.; Mizuno, N. Org. Lett. 2004, 6, 3577
32. Enguehard, C.; Renou, J.-L.; Collot, V.; Hervet, M.; Rault, S.; Gueiffier, A. J. Org. Chem. 2000, 65, 6572
33. Wu, Z.; Pan, Y.; Zhou, X. Synthesis 2011, 43, 2255
34. Kumar, J. S. D.; Ho, M. M.; Leung, J. M.; Toyokuni, T. Adv. Synth. Catal. 2002, 344, 1146
35. Lane, B. S.; Sames, D. Org. Lett. 2004, 6, 2897
36. Yanagisawa, S.; Sudo, T.; Noyori, R.; Itami, K. J. Am. Chem. Soc. 2006, 128, 11748
37. Labadie, S. S.; Teng, E. J. Org. Chem. 1994, 59, 4250
38. Ishikura, M.; Terashima, M. J. Org. Chem. 1994, 59, 2634
39. Lebrasseur, N.; Larrosa, I. J. Am. Chem. Soc. 2008, 130, 2926
40. Yang, S.-D.; Sun, C.-L.; Fang, Z.; Li, B.-J.; Li, Y.-Z.; Shi, Z.-J. Angew. Chem., Int. Ed. 2008, 47, 1473