Tandem one-pot construction of indoles via palladium and copper-catalyzed coupling reactions of the blaise reaction intermediate

Synthesis

Volumn 44, Issue 10, 2012, Pages 1464-1476

  Kim, Ju Hyun ^a   Lee, Sang Gi ^a  

^a Ewha Womans University   (South Korea)

Author keywords

Blaise reaction; copper; coupling; indoles; palladium; tandem reaction

Indexed keywords

BLAISE REACTION; C-N COUPLING; CHEMOSELECTIVE; COPPER IODIDE; COPPER-CATALYZED COUPLINGS; COUPLING REACTION; IN-SITU; INDOLE DERIVATIVES; INDOLES; INTERMOLECULAR COUPLING; N-ALKYLATION; N-ARYLATIONS; NOVEL ROUTE; ONE POT; ONE-POT SYNTHESIS; PALLADIUM CATALYST; PALLADIUM-CATALYZED; REFORMATSKY REAGENTS; TANDEM REACTION;

AROMATIC COMPOUNDS; CATALYSIS; CATALYSTS; COPPER; COUPLINGS; CYANIDES; ORGANOMETALLICS; PALLADIUM;

REACTION INTERMEDIATES;

1,2 DIHALOARENE DERIVATIVE; 1,2 DIHALOBENZENE; ACETIC ACID DERIVATIVE; ALKYL GROUP; BENZENE DERIVATIVE; COPPER; ETHYL 2 (TERT BUTYLDIMETHYLSILOXY) 2,3 DIHYDRO 1H PYRROLO[1,2 A]INDOLE 9 CARBOXYLATE; ETHYL 3 AMINO 2 (2 BROMOPHENYL) 6 CHLOROHEX 2 ENOATE; ETHYL 3 PHENYL 3 (PHENYLAMINO)PROP 2 ENOATE; ETHYL ALPHA BROMO ALPHA (2 BROMOPHENYL)ACETATE; ETHYL(2 BROMOPHENYL)AZEPAN 2 YLIDENEACETATE; ETHYL(2 BROMOPHENYL)PIPERIDIN 2 YLIDENEACETATE; ETHYL(2 BROMOPHENYL)PYRROLIDIN 2 YLIDENEACETATE; INDOLE DERIVATIVE; NITRILE; OMEGA CHLOROALKYL; PALLADIUM; REAGENT; REFORMATSKY REAGENT; UNCLASSIFIED DRUG; ZINC;

ALKYLATION; ARTICLE; ARYLATION; BLAISE REACTION INTERMEDIATE; CATALYSIS; CATALYST; CHEMICAL INTERACTION; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; ENANTIOSELECTIVITY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 84860747264     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0031-1289753     Document Type: Article

References (98)

1. Evans B E., Rittle K E., Bock M G., Dipardo R M., Freidinger R M., Whitter W L., Lundell G F., Veber D F., Anderson P S., J. Med. Chem. 1988 31 2235
2. Nicolaou K C., Pfefferkorn J A., Roecker A J., Cao G.-Q, Barluenga S, Mitchell H J., J. Am. Chem. Soc. 2000 122 9939
3. Kleeman A, Engel J, Kutscher B, Reichert D, Pharmaceutical Substances 4th ed. Thieme New York 2001
4. Humphrey G R., Kuethe J T., Chem. Rev. 2006 106 2875
5. For some recent reviews for indole synthesis, see:, Sundberg R J., Indoles Academic Press San Diego 1996
6. Gribble G W., J. Chem. Soc., Perkin Trans. 1 2000 1045
7. Gilchrist T L., J. Chem. Soc., Perkin Trans. 1 2001 2491
8. Joule J A., In Science of Synthesis Vol. 10 Thomas E J. Thieme Stuttgart 2000 361
9. For selected recent examples of indole synthesis, see:, Takeda A, Kamijo S, Yamamoto Y, J. Am. Chem. Soc. 2000 122 5662
10. Rutherford J L., Rainka M P., Buchwald S L., J. Am. Chem. Soc. 2002 124 15168
11. Siebeneicher H, Bytschkov I, Doye S, Angew. Chem. Int. Ed. 2003 42 3042
12. Taber D F., Tian W, J. Am. Chem. Soc. 2006 128 1058
13. Ackermann L, Synlett 2007 507
14. Ohno H, Ohta Y, Oishi S, Fujii N, Angew. Chem. Int. Ed. 2007 46 2295
15. Cariou K, Ronan B, Mignani S, Fensterbank L, Malacria M, Angew. Chem. Int. Ed. 2007 46 1881
16. Alex K, Tillack A, Schwarz N, Beller M, Angew. Chem. Int. Ed. 2008 47 2304
17. Kraus G A., Guo H, Org. Lett. 2008 10 3061
18. El Kaim L, Gizzi M, Grimaud L, Org. Lett. 2008 10 3417
19. Cui S.-L, Wang J, Wang Y.-G, J. Am. Chem. Soc. 2008 130 13526
20. For some recent reviews on Pd-catalyzed indole synthesis, see:, Li J J., Gribble G W., Palladium in Heterocyclic Chemistry Pergamon Oxford 2000
21. Cacchi S, Fabrizi G, Chem. Rev. 2005 105 2873
22. Larock R C., Yum E K., J. Am. Chem. Soc. 1991 113 6689
23. Larock R C., Yum E K., Refvik M D., J. Org. Chem. 1998 63 7652
24. Shen M, Li G, Lu B Z., Hossain A, Roschangar F, Farina V, Senanayake C H., Org. Lett. 2004 6 4129
25. Stuart D R., Bertrand-Laperle M, Burgess K M. N., Fagnou K, J. Am. Chem. Soc. 2008 130 16474
26. Houlden C E., Bailey C D., Ford J G., Gagné M R., Lloyd-Jones G C., Booker-Milburn K I., J. Am. Chem. Soc. 2008 130 10066
27. Shi Z, Zhang C, Li S, Pan D, Ding S, Cui Y, Jiao N, Angew. Chem. Int. Ed. 2009 48 4572
28. Thielges S, Meddah E, Bisseret P, Eustache J, Tetrahedron Lett. 2004 45 907
29. Fang Y.-Q, Lautens M, Org. Lett. 2005 7 3549
30. Fayol A, Fang Y.-Q, Lautens M, Org. Lett. 2006 8 4203
31. Fang Y.-Q, Lautens M, J. Org. Chem. 2008 73 538
32. Newman S G., Lautens M, J. Am. Chem. Soc. 2010 132 11416
33. Willis M C., Brace G N., Holmes I P., Angew. Chem. Int. Ed. 2005 44 403
34. Fletcher A J., Bax M N., Willis M C., Chem. Commun. 2007 4764
35. Barluenga J, Jiménez-Aquino A, Valdés C, Aznar F, Angew. Chem. Int. Ed. 2007 46 1529
36. Barluenga J, Jiménez-Aquino A, Aznar F, Valdés C, J. Am. Chem. Soc. 2009 131 4031
37. Wrütz S, Rakshit S, Neumann J J., Dröge T, Glorius F, Angew. Chem. Int. Ed. 2008 47 7230
38. Battistuzzi G, Cacchi S, Fabrizi G, Eur. J. Org. Chem. 2002 2671
39. Cacchi S, Fabrizi G, Parisi L M., Synthesis 2004 1889
40. Ho T.-L, Tandem Organic Reactions Wiley New York 1992
41. Tietze L F., Brasche G, Gericke K M., Domino Reactions in Organic Synthesis Wiley-VCH Weinheim 2006
42. Nicolaou K C., Edmonds D J., Bulger P G., Angew. Chem. Int. Ed. 2006 45 7134
43. Fürstner A, Angew. Chem. Int. Ed. 2009 48 1364
44. Parsons P J., Penkett C S., Shell A J., Chem. Rev. 1996 96 195
45. Feringa B L., Pineschi M, Arnold L A., Imbos R, de Vries A H. M., Angew. Chem. Int. Ed. 1997 36 2620
46. Alexakis A, Trevitt G P., Bernardinelli G, J. Am. Chem. Soc. 2001 123 4358
47. Mizutani H, Degrado S J., Hoveyda A H., J. Am. Chem. Soc. 2002 124 779
48. Agapiou K, Cauble D F., Krische M J., J. Am. Chem. Soc. 2004 126 4528
49. Greszler S N., Johnson J S., Angew. Chem. Int. Ed. 2009 48 3689
50. Greszler S N., Malinowski J T., Johnson J S., J. Am. Chem. Soc. 2010 132 17393
51. Haag B A., Zhang Z.-G, Li J.-S, Knochel P, Angew. Chem. Int. Ed. 2010 49 9513
52. Zhang Z.-G, Haag B A., Li J.-S, Knochel P, Synthesis 2011 23
53. Blaise E E., C. R. Hebd. Seances Acad. Sci. 1901 132 478
54. Blaise E E., C. R. Hebd. Seances Acad. Sci. 1901 132 987
55. Rathke M W., Weipert P, Zinc Enolates: The Reformatsky and Blaise Reaction, In Comprehensive Organic Reactions Vol. 2 Trost B M. Pergamon Oxford 1991 277-299
56. Rao H S. P., Rafi S, Padmavathy K, Tetrahedron 2008 64 8037
57. Chun Y S., Lee K K., Ko Y O., Shin H, Lee S.-g, Chem. Commun. 2008 5098
58. Ko Y O., Chun Y S., Park C.-L, Kim Y, Shin H, Ahn S, Hong J, Lee S.-g, Org. Biomol. Chem. 2009 7 1132
59. Chun Y S., Ko Y O., Shin H, Lee S.-g, Org. Lett. 2009 11 3414
60. Chun Y S., Ryu K Y., Ko Y O., Hong J Y., Hong J, Shin H, Lee S.-g, J. Org. Chem. 2009 74 7556
61. Ko Y O., Chun Y S., Kim Y, Kim S J., Shin H, Lee S.-g, Tetrahedron Lett. 2010 51 6893
62. Chun Y S., Ryu K Y., Kim J H., Shin H, Lee S.-g, Org. Biomol. Chem. 2011 9 1317
63. Chun Y S., Lee J H., Kim J H., Ko Y O., Lee S.-g, Org. Lett. 2011 13 6390
64. Jiang L, Buchwald S L., Metal-Catalyzed Cross Coupling Reactions 2nd ed., Vol. 2 Wiley-VCH Weinheim 2004 699-760
65. Muci A R., Buchwald S L., Top. Curr. Chem. 2002 219 131
66. Hartwig J F., In Handbook of Organopalladium Chemistry for Organic Synthesis Vol. 1 Wiley-Interscience New York 2002 1051-1096
67. Schlummer B, Scholz U, Adv. Synth. Catal. 2004 346 1599
68. Nakamura I, Yamamoto Y, Chem. Rev. 2004 104 2127
69. Kim J H., Lee S.-g, Org. Lett. 2011 13 1350
70. Shelby Q, Kataoka N, Mann G, Hartwig J, J. Am. Chem. Soc. 2000 122 10718
71. Hama T, Culkin D A., Hartwig J F., J. Am. Chem. Soc. 2006 128 4976
72. Barder T E., Walker S D., Martinelli J R., Buchwald S L., J. Am. Chem. Soc. 2005 127 4685
73. Huang X, Anderson K W., Zim D, Jian L, Klapars A, Buchwald S L., J. Am. Chem. Soc. 2003 125 6653
74. Feringa B L., Acc. Chem. Res. 2000 33 346
75. Kitamura M, Tokunaga M, Ohkuma T, Noyori R, Org. Synth. Coll. Vol. IX John Wiley & Sons London 1998 589
76. Yin J, Zhao M M., Huffman M A., McNamara J M., Org. Lett. 2002 4 3481
77. Lee S.-g, Zhang Y J., Song C E., Lee J K., Choi J H., Angew. Chem. Int. Ed. 2002 41 847
78. Lee S.-g, Zhang Y J., Org. Lett. 2002 4 2429
79. Zhang Y J., Park J H., Lee S.-g, Tetrahedron: Asymmetry 2004 15 2209
80. Hata T, Sano Y, Sugawara R, Matsumae A, Kanamori K, Shima T, Hoshi T, J. Antibiot. Ser. A 1956 9 141
81. Ewing J, Hughes G K., Ritchie E, Taylor W C., Nature 1952 169 618
82. Yoda N, Hirayama N, J. Med. Chem. 1993 36 1461
83. Goldbrunner M, Loidl G, Polossek T, Mannschreck A, von Angerer E, J. Med. Chem. 1997 40 3524
84. Peters R, Waldmeier P, Joncour A, Org. Process Res. Dev. 2005 9 508
85. Caddick S, Aboutayab K, Jenkins K, West R I., J. Chem. Soc., Perkin Trans. 1 1996 675
86. Bennasar M.-L, Roca T, Ferrando F, Org. Lett. 2004 6 759
87. Wang S.-F, Chuang C.-P, Tetrahedron Lett. 1997 38 7597
88. Shiue J.-S, Fang J.-M, J. Chem. Soc., Chem. Commun. 1993 1277
89. Ishikura M, Ida W, Yanada K, Tetrahedron 2006 62 1015
90. Verma A K., Kesharwani T, Singh J, Tandon V, Larock R C., Angew. Chem. Int. Ed. 2009 48 1138
91. Fuchibe K, Kaneko T, Mori K, Akiyama T, Angew. Chem. Int. Ed. 2009 48 8070
92. Kim J H., Shin H, Lee S.-g, J. Org. Chem. 2012 77 1560
93. Andrez J.-C, Beilstein J. Org. Chem. 2009 5; DOI: 10.3762/bjoc.5.33
94. Bernini R, Fabrizi G, Sferrazza A, Cacchi S, Angew. Chem. Int. Ed. 2009 48 8078
95. Moriwaki K, Satoh K, Takada M, Ishino Y, Ohno T, Tetrahedron Lett. 2005 46 7559
96. Sperotto E, Klink G P. M., Koten G, Vries J G., Dalton Trans. 2010 39 10338
97. Fotsch C, Bartberger M D., Bercot E A., Chen M, Cupples R, Emery M, Fretland J, Guram A, Hale C, Han N, Hickman D, Hungate R W., Hayashi M, Komorowski R, Liu Q, Matsumoto G, St. Jean D J., Ursu S, Véniant M, Xu G, Ye Q, Yuan C, Zhang J, Zhang X, Tu H, Wang M, J. Med. Chem. 2008 51 7953
98. Fraley M E., Garbaccio R M., Arrington K L., Hoffman W F., Tasber E S., Coleman P J., Buser C A., Walsh E S., Hamilton K, Fernandes C, Schaber M D., Lobell R B., Tao W, South V J., Yan Y, Kuo L C., Prueksaritanont T, Shu C, Torrent M, Heimbrook D C., Kohl N E., Huber H E., Hartman G D., Bioorg. Med. Chem. Lett. 2006 16 1775