Palladium-catalyzed direct C-2 arylation of indoles with aryl halides in aqueous medium

Synlett

Volumn 23, Issue 20, 2012, Pages 2992-2996

  Lu, Guo Ping ^a   Cai, Chun ^a  

^a NANJING UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

aqueous medium; arylation; green chemistry; indole; synthetic method

Indexed keywords

HALIDE; INDOLE DERIVATIVE; PALLADIUM;

AQUEOUS SOLUTION; ARTICLE; ARYLATION; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; GREEN CHEMISTRY; HYDROGEN BOND; HYDROPHILICITY; PROCESS OPTIMIZATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 84870057848     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0032-1317702     Document Type: Article

References (52)

1. Liu Y., McWhorter W. W. J. Am. Chem. Soc.: 2003; 125 4240
2. Higuchi K., Sato Y., Tsuchimochi M., Sugiura K., Hatori M., Kawasaki T. Org. Lett.: 2008; 11 197
3. Rohini R., Muralidhar Reddy P., Shanker K., Hu A., Ravinder V. Eur. J. Med. Chem.: 2010; 45 1200
4. Nahed F. A. E, Mona M. K., Mona K. S., Azza R. M., Galal S. H., Sara A. N. J. Chem. Pharm. Res.: 2011; 3 248
5. Cacchi S., Fabrizi G. Chem. Rev.: 2005; 105 2873
6. Rohini R., Shanker K., Reddy P. M., Sekhar V. C., Ravinder V. Arch. Pharm.: 2009; 342 533
7. Chauder B., Larkin A., Snieckus V. Org. Lett.: 2002; 4 815
8. Hartung C. G., Fecher A., Chapell B., Snieckus V. Org. Lett.: 2003; 5 1899
9. Dandu R., Tao M., Josef K. A., Bacon E. R., Hudkins R. L. J. Heterocycl. Chem.: 2007; 44 437
10. Hughes T. V., Emanuel S. L., OGrady H. R., Connolly P. J., Rugg C., Fuentes-Pesquera A. R., Karnachi P., Alexander R., Middleton S. A. Bioorg. Med. Chem. Lett.: 2008; 18 5130
11. Joucla L., Djakovitch L. Adv. Synth. Catal.: 2009; 351 673
12. Lebrasseur N., Larrosa I. Adv. Heterocycl. Chem.: 2012; 105 309
13. Boorman T. C., Larrosa I. In Progress in Heterocyclic Chemistry. Vol. 22 Gribble G., Joule J. Elsevier Amsterdam: 2011; 1
14. Sezen B., Sames D. J. Am. Chem. Soc.: 2006; 128 8364
15. Lane B. S., Brown M. A., Sames D. J. Am. Chem. Soc.: 2005; 127 8050
16. Bellina F., Calandri C., Cauteruccio S., Rossi R. Tetrahedron: 2007; 63 1970
17. Wang X., Gribkov D. V., Sames D. J. Org. Chem.: 2007; 72 1476
18. Huang Y., Lin Z., Cao R. Chem.-Eur. J.: 2011; 17 12706
19. Wang L., Yi W.-B, Cai C. Chem. Commun.: 2011; 47 806
20. Lane B. S., Sames D. Org. Lett.: 2004; 6 2897
21. Nikulin M., Lebedev A., Voskoboinikov A., Beletskaya I. Dokl. Chem. (Engl. Transl.): 2008; 423 326
22. Nadres E. T., Lazareva A., Daugulis O. J. Org. Chem.: 2010; 76 471
23. Deprez N. R., Kalyani D., Krause A., Sanford M. S. J. Am. Chem. Soc.: 2006; 128 4972
24. Lebrasseur N., Larrosa I. J. Am. Chem. Soc.: 2008; 130 2926
25. Jiao L., Bach T. J. Am. Chem. Soc.: 2011; 133 12990
26. Anastas P. T., Warner J. C. In Green Chemistry: Theory and Practice. Oxford University Press Oxford: 1998
27. Anastas P. T., Williamson T. In Green Chemistry, Frontiers in Benign Chemical Synthesis and Process. Oxford University of Press Oxford: 1998
28. Capello C., Fischer U., Hungerbuhler K. Green Chem.: 2007; 9 927
29. René O., Fagnou K. Org. Lett.: 2010; 12 2116
30. Nishikata T., Abela A. R., Lipshutz B. H. Angew. Chem. Int. Ed.: 2010; 49 781
31. Arockiam P. B., Fischmeister C., Bruneau C., Dixneuf P. H. Angew. Chem. Int. Ed.: 2010; 49 6629
32. Turner G. L., Morris J. A., Greaney M. F. Angew. Chem. Int. Ed.: 2007; 46 7996
33. Liston D. J., Lee Y. J., Scheidt W. R., Reed C. A. J. Am. Chem. Soc.: 1989; 111 6643
34. Albano V. G., Di Serio M., Monari M., Orabona I., Panunzi A., Ruffo F. Inorg. Chem.: 2002; 41 2672
35. Lafrance M., Fagnou K. J. Am. Chem. Soc.: 2006; 128 16496
36. Lipshutz B. H., Ghorai S. Aldrichimica Acta: 2008; 41 59
37. Lipshutz B. H., Ghorai S. Aldrichimica Acta: 2012; 45 3
38. Lu G.-P, Cai C. Colloid. Surface. Physicochem. Eng. Aspect.: 2010; 355 193
39. Lin L., Li Y., Zhang S., Li S. Synlett: 2011; 1779
40. Shinde M. M., Bhagwat S. S. Colloid. Surface. Physicochem. Eng. Aspect.: 2011; 380 201
41. Park K., Bae G., Park A., Kim Y., Choe J., Song K. H., Lee S. Tetrahedron Lett.: 2011; 52 576
42. Lessi M., Masini T., Nucara L., Bellina F., Rossi R. Adv. Synth. Catal.: 2011; 353 501
43. Duplais C., Krasovskiy A., Wattenberg A., Lipshutz B. H. Chem. Commun.: 2010; 46 562
44. Chanda A., Fokin V. V. Chem. Rev.: 2009; 109 725
45. Narayan S., Muldoon J., Finn M. G., Fokin V. V., Kolb H. C., Sharpless K. B. Angew. Chem. Int. Ed.: 2005; 44 3275
46. Zhang H.-B, Liu L., Chen Y.-J, Wang D., Li C.-J. Eur. J. Org. Chem.: 2006; 869
47. Torihata A., Kuroda C. Synlett: 2011; 2035
48. Dwars T., Paetzold E., Oehme G. Angew. Chem. Int. Ed.: 2005; 44 7174
49. Morawetzm H. In Catalysis and Inhibition in Solutions of Synthetic Polymers and in Micellar Solutions. Vol. 20 Eley H. P. D. D, Paul B. W. Academic Press San Diego: 1969; 341
50. Lindström U. M. Chem. Rev.: 2002; 102 2751
51. Lu G.-P, Zeng L.-Y, Cai C. Green Chem.: 2011; 13 998
52. Lu G.-P, Cai C. J. Chem. Res.: 2011; 35 547