1 Palladium-catalyzed Coupling Reactions <strong>of</strong> Indoles 67 [21] A. N. C. Lötter, R. Pathak, T. S. Sello, M. A. Fern<strong>and</strong>es, W. A. L. Otterlo, C. B. de Koning, Terahedron 2007, 63, 2263-2274. [22] M. Menes-Arzate, R. Martínez, R. Cruz-Almanza, J. M. Muchowski, Y. M. Osornio, L. D. Mir<strong>and</strong>a, J. Org. Chem. 2004, 69, 4001-4004. [23] a) C. B. de Koning, J. P. Michael, A. L. Rousseau, J. Chem. Soc., Perkin Trans. 1 2000, 787-797; b) C. B. de Koning, J. P. Michael, A. L. Rousseau, J. Chem. Soc., Perkin Trans. 1 2000, 1705-1713. [24] M. A. Campo, H. Zhang, T. Yao, A. Ibdah, R. D. McCulla, Q. Huang, J. Zhao, W. S. Jenks, R. C. Larock, J. Am. Chem. Soc. 2007, 129, 6298-6307. [25] M. A. Kotharé, J. Okh<strong>and</strong>a, J. W. Lockman, Y. Quian, M. A. Blaskovich, S. Sebti, A. D. Hamilton, Tetrahedron 2000, 56, 9833-9841. [26] S. W. Wright, D. L. Hagemann, L. D. McClure, J. Org. Chem. 1994, 59, 6095-6097. [27] M. Prieto, S. Mayor, K. Rodriguez, P. Lloyd-Williams, E. Giralt, J. Org. Chem. 2007, 72, 1047-1050. [28] For substrate racemization, see: a) N. L. Benoiton, Chemistry <strong>of</strong> Peptide Synthesis; CRC Press: Boca Raton, 2006; b) P. Lloyed-Williams, F. Albericio, E. Giralt, Chemical Approaches to the Synthesis <strong>of</strong> Peptides <strong>and</strong> Proteins; CRC Press: Boca Raton, 1997. [29] For indolyl boronic acids, see: M. P. Moyer, J. F. Shiurba, H. Rapoport, J. Org. Chem. 1986 , 51, 5106-5110. [30] For interests in chloropeptins, see: a) T. Shinohara, H. B. Deng, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2005, 127, 7334-7336; b) H. B. Deng, J. K. Jung, T. Liu, K. W. Kuntz, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2003, 125, 9032-9034. [31] N. Kudo, M. Perseghini, G. C. Fu, Angew. Chem. Int. Ed. 2006, 45, 1282- 1284; Angew. Chem. 2006, 118, 1304-1306. [32] For Suzuki-Miyaura reactions <strong>of</strong> nitrogen heterocycles, see: a) T. E. Barder, S. D. Walker, J. R. Martinelli, S. L. Buchwald, J. Am. Chem. Soc. 2005, 127, 4685-4696; b) A. E. Thompson, G. Hughes, A. S. Batsanov, M. R. Bryce, P. R. Parry, B. Tarbit, J. Org. Chem. 2005, 70, 388-390; c) I. Kondolff, H. Doucet, M. Santelli, Synlett 2005, 2057-2061; d) T. E. Barder, S. L. Buchwald, Org. Lett. 2004, 6, 2649-2652.
1 Palladium-catalyzed Coupling Reactions <strong>of</strong> Indoles 68 [33] For direct cross coupling reactions dealing with heteroaryl moieties with unprotected NH2 groups, see: a) T. Itoh, T. Mase, Tetrahedron Lett. 2005, 46, 3573-3577; b) T. Itoh, K. Sato; T. Mase, Adv. Synth. Catal. 2004, 346, 1859-1867; c) P. Gunda, L. M. Russon, M. K. Lakshman, Angew. Chem. Int. Ed. 2004, 43, 6372-6377; Angew. Chem. 2004, 116, 6532-6537; d) L. A. Agr<strong>of</strong>oglio, I. Gillaizeau, Y. Saito, Chem. Rev. 2003, 103, 1875-1916; e) T. Tagata, M. Nishida, J. Org. Chem. 2003, 68, 9412-9415; f) M. Feuerstein, H. Doucet, M. Santelli, J. Organomet. Chem. 2003, 687, 327-336. [34] K. L. Billingsley, K. W. Anderson, S. L. Buchwald, Angew. Chem. Int. Ed. 2006, 45, 3484-3488; Angew. Chem. 2006, 118, 3564-3568. [35] S. Wagaw, S. L. Buchwald, J. Org. Chem. 1996, 61, 7240-7241. [36] a) S. Caron, S. S. Masset, D. E. Bogle, M. J. Castaldi, T. F. Braish, Org. Process Res. Dev. 2001, 5, 254-256; b) J. A. Miller, R. P. Farrell, Tetrahedron Lett. 1998, 39, 6441-6444. [37] K. Billingsley, S. L. Buchwald, J. Am. Chem. Soc. 2007, 129, 3358-3366. [38] a) C. Johnson, G. Stemp, N. Anh<strong>and</strong>, S. Stephen, T. Gallagher, Synlett 1998, 1025-1027; b) Y. Yang, A. R. Martin, Heterocycles 1992, 34, 1395- 1398. [39] G. Miao, P. Ye, L. Yu, C. M. Baldino, J. Org. Chem. 2005, 70, 2332-2334. [40] a) G. Y. Li, J. Org. Chem. 2002, 67, 3643-3650; b) G. Y. Li, Angew. Chem. Int. Ed. 2001, 40, 1513-1516; Angew. Chem. 2001, 113, 1561-1564; c) G. Y. Li, G. Zheng, A. F. Noonan, J. Org. Chem. 2001, 66, 8677-8688. [41] a) M. Larhed, C. Moberg, A. Hallberg, Acc. Chem. Res. 2002, 35, 717-727; b) D. Villemin, M. H. Gómez-Escalonilla, J. Saint-Clair, Tetrahedron Lett. 2001, 42, 635-637; c) C. G. Blettner, W. A. König, W. Stenzel, T. Schotten, J. Org. Chem. 1999, 64, 3885-3890. [42] N. E. Leadbeater, M. Marco, Org. Lett. 2002, 4, 2973-2976. [43] N. E. Leadbeater, M. Marco, Angew. Chem. Int. Ed. 2003, 42, 1407-1409; Angew. Chem. 2003, 115, 1445-1447. [44] For recent reviews on solid phase <strong>synthesis</strong>, see: a) R. E. Dolle, J. Comb. Chem. 2003, 5, 693-753; b) V. Krchñák, M. W. Holladay, Chem. Rev. 2002, 102, 61-91. [45] a) S. Bräse, J. H. Kirchh<strong>of</strong>f, J. Köbberling, Tetrahedron 2003, 69, 885-939; b) B. A. Lorsbach, M. J. Kurth, Chem. Rev. 1999, 99, 1549-1581; c) S. R.
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Preface The search for drugs is an
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Synthesis of Potential 5-HT 6 Recep
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Synthesis of Potential 5-HT 6 Recep
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Synthesis of Indole-2,3-dicarboxyla
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8 7 N R N R OH CO2Et CO2Et OH indol
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