Recent Advances in the C2 and C3 Regioselective Direct Arylation of Indoles

Advances in Heterocyclic Chemistry

Volumn 105, Issue , 2012, Pages 309-351

  Lebrasseur, Nathalie ^a   Larrosa, Igor ^a  

^a QUEEN MARY UNIVERSITY OF LONDON   (United Kingdom)

Author keywords

Arylation; C H activation; Decarboxylative coupling; Indole; Palladium catalysis

Indexed keywords

EID: 84857431566     PISSN: 00652725     EISSN: None     Source Type: Book Series    
DOI: 10.1016/B978-0-12-396530-1.00004-8     Document Type: Chapter

References (81)

1. Sundberg R.J. The Chemistry of Indoles 1970, Academic Press, New York.
2. Brown R.K. Indoles 1972, Wiley-Interscience, New York. W.J. Houlihan (Ed.).
3. Hino T., Nakagawa M. Heterocycles 1977, 8:743.
4. T. Itahara and T. Sakakibara, Synthesis, 607 (1978).
5. Itahara T. Synthesis 1979, 151.
6. Szabo-Pusztay K., Szabo L. Synthesis 1979, 276.
7. Itahara T. J. Chem. Soc., Chem. Commun. 1981, 254.
8. Akita Y., Inoue A., Yamamonto K., Ohta A., Kurihara T., Shimizu M. Heterocycles 1985, 23:2327.
9. Akita Y., Itagaki Y., Takizawa S., Ohta A. Chem. Pharm. Bull. 1989, 37:1477.
10. Sundberg R.J. Indoles (Best Synthetic Method) 1996, Academic Press.
11. Catellani M., Frigani F., Rangoni A. Angew. Chem. Int. Ed. 1997, 36:119.
12. Stanforth S.P. Tetrahedron 1998, 54:263.
13. Joules J.A. Indole and its derivatives in science of synthesis. Houben-Weyl Methods of Molecular Transformations 2000, Vol. 10. Stuttgart, Thieme, Chap. 10.13.
14. Hassan J., Sévignon M., Gozzi C., Schulz E., Lemaire M. Chem. Rev. 2002, 102:1359.
15. Catelanni M., Mealli C., Motti E., Paoli P., Perez-Carreno E., Pregosine P.S. J. Am. Chem. Soc. 2002, 124:4336.
16. Ferreira E.M., Stoltz B.M. J. Am. Chem. Soc. 2003, 125:9578.
17. Catelanni M. Synlett 2003, 298.
18. Lane B.S., Sames D. Org. Lett. 2004, 6:2897.
19. Cacchi S., Fabrizi G. Chem. Rev. 2005, 105:2873.
20. Chen F.-R., Huang J. Chem. Rev. 2005, 105:4671.
21. Wang X., Lane B.S., Sames D. J. Am. Chem. Soc. 2005, 127:4996.
22. Lane B.S., Brown M.A., Sames D. J. Am. Chem. Soc. 2005, 127:8050.
23. Bressy C., Alberico D., Lautens M. J. Am. Chem. Soc. 2005, 127:13148.
24. Deprez N.R., Kalyani D., Krause A., Sanford M.S. J. Am. Chem. Soc. 2006, 128:4972.
25. Bellina F., Cauteruccio S., Rossi R. Eur. J. Org. Chem. 2006, 1379.
26. Touré B.B., Lane B.S., Sames D. Org. Lett. 2006, 8:1979.
27. Baudoin O. Angew. Chem. Int. Ed. 2007, 46:1374.
28. Djakovitch L., Rouge P., Zaidi R. Catal. Commun. 2007, 8:1561.
29. Alberico D., Scott M.E., Lautens M. Chem. Rev. 2007, 107:174.
30. Stuart D.R., Villemure E., Fagnou K. J. Am. Chem. Soc. 2007, 129:12072.
31. Wang X., Gribkov D.V., Sames D. J. Org. Chem. 2007, 72:1476.
32. Bergman R.G. Nature 2007, 446:391.
33. Dwight T.A., Rue N.R., Charyk D., Josselyn R., DeBoef B. Org. Lett. 2007, 9:3137.
34. Stuart D.R., Fagnou K. Science 2007, 316:1172.
35. Bellina F., Calandri C., Cauteruccio S., Rossi R. Tetrahedron 2007, 63:1970.
36. Zang Z., Hu Z., Yu Z., Lei P., Chi H., Wang Y., He R. Tetrahedron Lett. 2007, 48:2415.
37. Yang S.-D., Sun C.-L., Fang Z., Li B.-J., Li Y.-Z., Shi Z.-J. Angew. Chem. Int. Ed. 2008, 47:1473.
38. Goossen L.J., Rodriguez N., Goossen K. Angew. Chem. Int. Ed. 2008, 47:3100.
39. Bonesi S.M., Fagnoni M., Albini A. Angew. Chem. Int. Ed. 2008, 47:10022.
40. Lebrasseur N., Larrosa I. J. Am. Chem. Soc. 2008, 130:2926.
41. Phipps R.J., Grimster N.P., Gaunt M.J. J. Am. Chem. Soc. 2008, 130:8172.
42. Blaszykowski C., Aktoudianakis E., Alberico D., Bressy C., Hulcoop D.G., Jafarpour F., Joushaghani A., Laleu B., Lautens M. J. Org. Chem. 2008, 73:1888.
43. Bellina F., Benelli R., Rossi R. J. Org. Chem. 2008, 73:5529.
44. Zhao J., Zhang Y., Cheng K. J. Org. Chem. 2008, 73:7428.
45. Kirchber S., Vogler T., Studer A. Synlett 2008, 2841.
46. Nandurkar N.S., Bhanushali M.J., Bhor M.D., Bhanage B.M. Tetrahedron Lett. 2008, 49:1045.
47. Cusati G., Djakovitch L. Tetrahedron Lett. 2008, 49:2499.
48. Potavathri S., Dumas A.S., Dwight T.A., Naumiec G.R., Hammann J.M., DeBoef B. Tetrahedron Lett. 2008, 49:4050.
49. Verma A.K., Kesharwani T., Singh J., Tandon V., Larock R.C. Angew. Chem. Int. Ed. 2009, 48:1138.
50. Kirchberg S., Fröhlich R., Studer A. Angew. Chem. Int. Ed. 2009, 48:4235.
51. Bandini M., Eichholzer A. Angew. Chem. Int. Ed. 2009, 48:9608.
52. Ackermann L., Rubén V., Kapdi A.R. Angew. Chem. Int. Ed. 2009, 48:9792.
53. Joucla L., Djakovitch L. Adv. Synth. Catal. 2009, 351:673.
54. Miyasaka M., Fukushima A., Satoh T., Hirano K., Miura M. Chem. Eur. J. 2009, 15:3674.
55. Huestis M.P., Fagnou K. Org. Lett. 2009, 11:1357.
56. Cornella J., Lu P., Larrosa I. Org. Lett. 2009, 11:5506.
57. Sagnes C., Fournet G., Joseph B. Synlett 2009, 433.
58. Ackermann L., Barfuesser S. Synlett 2009, 808.
59. Barbero N., SanMartin R., Domínguez E. Tetrahedron Lett. 2009, 50:2129.
60. Joucla L., Batail N., Djakovitch L. Adv. Synth. Catal. 2010, 352:2929.
61. Wang L., Han Z., Fan R. Adv. Synth. Catal. 2010, 352:3230.
62. Ruiz-Rodríguez J., Albericio F., Lavilla R. Chem. Eur. J. 2010, 16:1124.
63. Jazzar R., Hitce J., Renaudat A., Sofack-Kreutzer J., Baudoin O. Chem. Eur. J. 2010, 16:2654.
64. Zhou J., Hu P., Zhang M., Huang S., Wang M., Su W. Chem. Eur. J. 2010, 16:5876.
65. J.A. Ashenhurst, Chem. Soc. Rev., 39, 540. (2010).
66. Potavathri S., Pereira K.C., Gorelsky S.I., Pike A., LeBris A.P., DeBoef B. J. Am. Chem. Soc. 2010, 132:14676.
67. Liégault B., Petrov I., Gorelsky S.I., Fagnou K. J. Org. Chem. 2010, 75:1047.
68. Satoh T., Miura M. Synthesis 2010, 20:3395.
69. Wang Z., Li K.Z., Zhao D.B., Lan J.B., You J.S. Angew. Chem. Int. Ed. 2011, 50:5365.
70. Potavathri S., Kantak A., DeBoef B. Chem. Commun. 2011, 47:4679.
71. Wang L., Yi W.-B., Cai C. Chem. Commun. 2011, 47:806.
72. Zhao D.B., You J.S., Hu C.W. Chem. Eur. J. 2011, 17:5466.
73. Yamaguchi A.D., Mendal D., Yamagushi J., Itami K. Chem. Lett. 2011, 40:555.
74. Yeung C.S., Dong V.M. Chem. Rev. 2011, 111:1215.
75. Ackerman L. Chem. Rev. 2011, 111:1315.
76. Liu C., Zhang H., Shi W., Lei A.W. Chem. Rev. 2011, 111:1780.
77. Pintori D.G., Greaney M.F. J. Am. Chem. Soc. 2011, 133:1209.
78. Nadres E.T., Lazareva A., Daugulis O. J. Org. Chem. 2011, 76:471.
79. Lapointe D., Markiewicz T., Whipp C.J., Toderian A., Fagnou K. J. Org. Chem. 2011, 76:749.
80. Gong X., Song G., Zhang H., Li X. Org. Lett. 2011, 13:1766.
81. Boorman T.C., Larrosa I. Progress in Heterocyclic Chemistry 2011, Vol. 22:1. Elsevier Ltd, Oxford.