FEATURE ARTICLE
Int. Ed. 2003, 42, 3042. (d) Taber, D. F.; Tian, W. J. Am.
Tandem One-Pot Construction of Indoles
1475
(15) (a) Blaise, E. E. C. R. Hebd. Seances Acad. Sci. 1901, 132,
478. (b) Blaise, E. E. C. R. Hebd. Seances Acad. Sci. 1901,
132, 987. (c) Rathke, M. W.; Weipert, P. Zinc Enolates: The
Reformatsky and Blaise Reaction, In Comprehensive
Organic Reactions, Vol. 2; Trost, B. M., Ed.; Pergamon:
Oxford, 1991, 277–299. (d) Rao, H. S. P.; Rafi, S.;
Padmavathy, K. Tetrahedron 2008, 64, 8037.
(16) (a) Chun, Y. S.; Lee, K. K.; Ko, Y. O.; Shin, H.; Lee, S.-g.
Chem. Commun. 2008, 5098. (b) 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. (c) Chun, Y. S.; Ko, Y.
O.; Shin, H.; Lee, S.-g. Org. Lett. 2009, 11, 3414. (d)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. (e) Ko, Y. O.;
Chun, Y. S.; Kim, Y.; Kim, S. J.; Shin, H.; Lee, S.-g.
Tetrahedron Lett. 2010, 51, 6893. (f) Chun, Y. S.; Ryu, K.
Y.; Kim, J. H.; Shin, H.; Lee, S.-g. Org. Biomol. Chem.
2011, 9, 1317. (g) Chun, Y. S.; Lee, J. H.; Kim, J. H.; Ko, Y.
O.; Lee, S.-g. Org. Lett. 2011, 13, 6390.
(17) (a) Jiang, L.; Buchwald, S. L. Metal-Catalyzed Cross
Coupling Reactions, 2nd ed., Vol. 2; Wiley-VCH:
Weinheim, 2004, 699–760. (b) Muci, A. R.; Buchwald, S. L.
Top. Curr. Chem. 2002, 219, 131. (c) Hartwig, J. F. In
Handbook of Organopalladium Chemistry for Organic
Synthesis, Vol. 1; Wiley-Interscience: New York, 2002,
1051–1096. (d) Schlummer, B.; Scholz, U. Adv. Synth.
Catal. 2004, 346, 1599. (e) Nakamura, I.; Yamamoto, Y.
Chem. Rev. 2004, 104, 2127.
(18) Kim, J. H.; Lee, S.-g. Org. Lett. 2011, 13, 1350.
(19) (a) Shelby, Q.; Kataoka, N.; Mann, G.; Hartwig, J. J. Am.
Chem. Soc. 2000, 122, 10718. (b) Hama, T.; Culkin, D. A.;
Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 4976.
(20) Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S.
L. J. Am. Chem. Soc. 2005, 127, 4685.
(21) Huang, X.; Anderson, K. W.; Zim, D.; Jian, L.; Klapars, A.;
Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 6653.
(22) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346.
(23) Kitamura, M.; Tokunaga, M.; Ohkuma, T.; Noyori, R. Org.
Synth. Coll. Vol. IX; John Wiley & Sons: London, 1998, 589.
(24) Yin, J.; Zhao, M. M.; Huffman, M. A.; McNamara, J. M.
Org. Lett. 2002, 4, 3481.
(25) (a) Lee, S.-g.; Zhang, Y. J.; Song, C. E.; Lee, J. K.; Choi, J.
H. Angew. Chem. Int. Ed. 2002, 41, 847. (b) Lee, S.-g.;
Zhang, Y. J. Org. Lett. 2002, 4, 2429. (c)Zhang, Y. J.;Park,
J. H.; Lee, S.-g. Tetrahedron: Asymmetry 2004, 15, 2209.
(26) (a) Hata, T.; Sano, Y.; Sugawara, R.; Matsumae, A.;
Kanamori, K.; Shima, T.; Hoshi, T. J. Antibiot. Ser. A 1956,
9, 141. (b) Ewing, J.; Hughes, G. K.; Ritchie, E.; Taylor, W.
C. Nature 1952, 169, 618. (c) Yoda, N.; Hirayama, N. J.
Med. Chem. 1993, 36, 1461. (d)Goldbrunner, M.;Loidl, G.;
Polossek, T.; Mannschreck, A.; von Angerer, E. J. Med.
Chem. 1997, 40, 3524.
(27) (a) Peters, R.; Waldmeier, P.; Joncour, A. Org. Process Res.
Dev. 2005, 9, 508. (b) Caddick, S.; Aboutayab, K.; Jenkins,
K.; West, R. I. J. Chem. Soc., Perkin Trans. 1 1996, 675.
(c) Bennasar, M.-L.; Roca, T.; Ferrando, F. Org. Lett. 2004,
6, 759. (d) Wang, S.-F.; Chuang, C.-P. Tetrahedron Lett.
1997, 38, 7597. (e) Shiue, J.-S.; Fang, J.-M. J. Chem. Soc.,
Chem. Commun. 1993, 1277. (f) Ishikura, M.; Ida, W.;
Yanada, K. Tetrahedron 2006, 62, 1015. (g) Verma, A. K.;
Kesharwani, T.; Singh, J.; Tandon, V.; Larock, R. C. Angew.
Chem. Int. Ed. 2009, 48, 1138. (h) Fuchibe, K.; Kaneko, T.;
Mori, K.; Akiyama, T. Angew. Chem. Int. Ed. 2009, 48,
8070.
Chem. Soc. 2006, 128, 1058. (e) Ackermann, L. Synlett
2007, 507. (f) Ohno, H.; Ohta, Y.; Oishi, S.; Fujii, N. Angew.
Chem. Int. Ed. 2007, 46, 2295. (g) Cariou, K.; Ronan, B.;
Mignani, S.; Fensterbank, L.; Malacria, M. Angew. Chem.
Int. Ed. 2007, 46, 1881. (h) Alex, K.; Tillack, A.; Schwarz,
N.; Beller, M. Angew. Chem. Int. Ed. 2008, 47, 2304.
(i) Kraus, G. A.; Guo, H. Org. Lett. 2008, 10, 3061.
(j) El Kaim, L.; Gizzi, M.; Grimaud, L. Org. Lett. 2008, 10,
3417. (k) Cui, S.-L.; Wang, J.; Wang, Y.-G. J. Am. Chem.
Soc. 2008, 130, 13526.
(4) For some recent reviews on Pd-catalyzed indole synthesis,
see: (a) Li, J. J.; Gribble, G. W. Palladium in Heterocyclic
Chemistry; Pergamon: Oxford, 2000. (b) Cacchi, S.;
Fabrizi, G. Chem. Rev. 2005, 105, 2873.
(5) (a) Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113,
6689. (b) Larock, R. C.; Yum, E. K.; Refvik, M. D. J. Org.
Chem. 1998, 63, 7652. (c) Shen, M.; Li, G.; Lu, B. Z.;
Hossain, A.; Roschangar, F.; Farina, V.; Senanayake, C. H.
Org. Lett. 2004, 6, 4129.
(6) (a) Stuart, D. R.; Bertrand-Laperle, M.; Burgess, K. M. N.;
Fagnou, K. J. Am. Chem. Soc. 2008, 130, 16474. For a
similar result for the Pd(II)-catalyzed preparation of indoline
using a urea moiety as the activating group, see:
(b) 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. (c) Shi, Z.; Zhang, C.; Li, S.; Pan, D.;
Ding, S.; Cui, Y.; Jiao, N. Angew. Chem. Int. Ed. 2009, 48,
4572.
(7) (a) Thielges, S.; Meddah, E.; Bisseret, P.; Eustache, J.
Tetrahedron Lett. 2004, 45, 907. (b) Fang, Y.-Q.; Lautens,
M. Org. Lett. 2005, 7, 3549. (c) Fayol, A.; Fang, Y.-Q.;
Lautens, M. Org. Lett. 2006, 8, 4203. (d) Fang, Y.-Q.;
Lautens, M. J. Org. Chem. 2008, 73, 538. (e) Newman, S.
G.; Lautens, M. J. Am. Chem. Soc. 2010, 132, 11416.
(8) (a) Willis, M. C.; Brace, G. N.; Holmes, I. P. Angew. Chem.
Int. Ed. 2005, 44, 403. (b) Fletcher, A. J.; Bax, M. N.;
Willis, M. C. Chem. Commun. 2007, 4764.
(9) (a) Barluenga, J.; Jiménez-Aquino, A.; Valdés, C.; Aznar, F.
Angew. Chem. Int. Ed. 2007, 46, 1529. (b) Barluenga, J.;
Jiménez-Aquino, A.; Aznar, F.; Valdés, C. J. Am. Chem.
Soc. 2009, 131, 4031.
(10) Wrütz, S.; Rakshit, S.; Neumann, J. J.; Dröge, T.; Glorius, F.
Angew. Chem. Int. Ed. 2008, 47, 7230.
(11) (a) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem.
2002, 2671. (b) Cacchi, S.; Fabrizi, G.; Parisi, L. M.
Synthesis 2004, 1889.
(12) (a) Ho, T.-L. Tandem Organic Reactions; Wiley: New York,
1992. (b) Tietze, L. F.; Brasche, G.; Gericke, K. M. Domino
Reactions in Organic Synthesis; Wiley-VCH: Weinheim,
2006. (c) Nicolaou, K. C.; Edmonds, D. J.; Bulger, P. G.
Angew. Chem. Int. Ed. 2006, 45, 7134. (d) Fürstner, A.
Angew. Chem. Int. Ed. 2009, 48, 1364. (e) Parsons, P. J.;
Penkett, C. S.; Shell, A. J. Chem. Rev. 1996, 96, 195.
(13) (a) Feringa, B. L.; Pineschi, M.; Arnold, L. A.; Imbos, R.;
de Vries, A. H. M. Angew. Chem. Int. Ed. 1997, 36, 2620.
(b) Alexakis, A.; Trevitt, G. P.; Bernardinelli, G. J. Am.
Chem. Soc. 2001, 123, 4358. (c) Mizutani, H.; Degrado, S.
J.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 779.
(d) Agapiou, K.; Cauble, D. F.; Krische, M. J. J. Am. Chem.
Soc. 2004, 126, 4528. (e) Greszler, S. N.; Johnson, J. S.
Angew. Chem. Int. Ed. 2009, 48, 3689. (f) Greszler, S. N.;
Malinowski, J. T.; Johnson, J. S. J. Am. Chem. Soc. 2010,
132, 17393.
(14) (a) Haag, B. A.; Zhang, Z.-G.; Li, J.-S.; Knochel, P. Angew.
Chem. Int. Ed. 2010, 49, 9513. (b) Zhang, Z.-G.; Haag, B.
A.; Li, J.-S.; Knochel, P. Synthesis 2011, 23.
(28) Kim, J. H.; Shin, H.; Lee, S.-g. J. Org. Chem. 2012, 77,
1560.
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