18.11.2012 Views

synthesis and catalytic functionalization of biologically active indoles

synthesis and catalytic functionalization of biologically active indoles

synthesis and catalytic functionalization of biologically active indoles

SHOW MORE
SHOW LESS

Create successful ePaper yourself

Turn your PDF publications into a flip-book with our unique Google optimized e-Paper software.

J. Org. Chem. 2001, 66, 6339–6343; r) Y. Fukumoto, H. Asai, M. Shimizu,<br />

N. Chatani, J. Am. Chem. Soc. 2007, DOI: 10.1021/ja075484e. Iridium:<br />

s) R.-Y. Lai, K. Surekha, A. Hayashi, F. Ozawa, Y.-H. Liu, S.-M. Peng, S.-T.<br />

Liu, Organometallics 2007, 26, 1062–1068. Pd: t) T. Shimada, G. B. Bajracharya,<br />

Y. Yamamoto, Eur. J. Org. Chem. 2005, 59–62; u) T. Shimada, Y.<br />

Yamamoto, J. Am. Chem. Soc. 2002, 124, 12670–12671. Platinum: v) J.-J.<br />

Brunet, N. Châu Chu, O. Diallo, S. Vincendeau, J. Mol. Catal. 2005, 240,<br />

245–248. Silver: w) Y. Luo, Z. Li, C.-J. Li, Org. Lett. 2005, 7, 2675–2678.<br />

Gold: x) R. A. Widenhoefer, X. Han, Eur. J. Org. Chem. 2006, 4555–4563;<br />

y) E. Mizushima, T. Hayashi, M. Tanaka, Org. Lett. 2003, 5, 3349–3352.<br />

[4] G. V. Shanbhag, S. M. Kumbar, T. Joseph, S. B. Halligudi, Tetrahedron Lett.<br />

2006, 47, 141–143.<br />

[5] a) S. Breitenlechner, M. Fleck, T. E. Müller, A. Suppan, J. Mol. Catal. 2004,<br />

214, 175–179; for intermolecular heterogeneous Zn-catalyzed hydroaminations<br />

<strong>of</strong> alkynes, see: b) G. V. Shanbhag, S. B. Halligudi, J. Mol.<br />

Catal. 2004, 222, 223–228; c) J. Bodis, T. E. Müller, J. A. Lercher, Green<br />

Chem. 2003, 5, 227–231.<br />

[6] a) K. Takaki, S. Koizumi, Y. Yamamoto, K. Komeyama, Tetrahedron Lett.<br />

2006, 47, 7335–7337; b) A. L. Odom, Dalton Trans. 2005, 225–233; c) N.<br />

Hazari, P. Mountford, Acc. Chem. Res. 2005, 38, 839–849; d) A. Heutling,<br />

F. Pohlki, S. Doye, Chem. Eur. J. 2004, 10, 3059–3071; e) C. Li, R. K. Thomson,<br />

B. Gillon, B. O. Patrick, L. L. Schafer, Chem. Commun. 2003, 2462–<br />

2463; f) L. Ackermann, Organometallics 2003, 22, 4367–4368; g) Y. Shi,<br />

C. Hall, J. T. Ciszewski, C. Cao, A. L. Odom, Chem. Commun. 2003, 586–<br />

587; h) Z. Zhang, L. L. Schafer, Org. Lett. 2003, 5, 4733–4736; i) J. E. Hill,<br />

R. D. Pr<strong>of</strong>ilet, P. E. Fanwick, I. P. Rothwell, Angew. Chem. 1990, 102, 713–<br />

715; Angew. Chem. Int. Ed. Engl. 1990, 29, 664–665.<br />

[7] a) A. Tillack, V. Khedkar, H. Jiao, M. Beller, Eur. J. Org. Chem. 2005, 5001–<br />

5012; b) A. Tillack, H. Jiao, I. Garcia Castro, C. G. Hartung, M. Beller,<br />

Chem. Eur. J. 2004, 10, 2409–2420.<br />

[8] a) V. Khedkar, A. Tillack, M. Michalik, M. Beller, Tetrahedron 2005, 61,<br />

7622–7631; b) V. Khedkar, A. Tillack, M. Michalik, M. Beller, Tetrahedron<br />

2005, 61, 7622–7631; c) V. Khedkar, A. Tillack, M. Michalik, M. Beller, Tetrahedron<br />

Lett. 2004, 45, 3123–3126; d) A. Tillack, H. Jiao, I. G. Castro,<br />

C. G. Hartung, M. Beller, Chem. Eur. J. 2004, 10, 2409–2420; e) L. Ackermann,<br />

R. Born, Tetrahedron Lett. 2004, 45, 9541–9544; f) C. Cao, Y. Shi,<br />

A. L. Odom, Org. Lett. 2002, 4, 2853–2856; g) P. T. Walsh, M. J. Carney,<br />

R. G. Bergman, J. Am. Chem. Soc. 1991, 113, 6343–6345.<br />

[9] K. Alex, A. Tillack, N. Schwarz, M. Beller, unpublished results.<br />

[10] a) N. Meyer, K. Lçhnwitz, A. Zulys, P. W. Roesky, M. Dochnahl, S. Blechert,<br />

Organometallics 2006, 25, 3730–3734; b) A. Zulys, M. Dochnahl, D. Hollmann,<br />

K. Lçhnwitz, J.-S. Herrmann, P. W. Roesky, S. Blechert, Angew.<br />

Chem. 2005, 117, 7972–7976; Angew. Chem. Int. Ed. 2005, 44, 7794–<br />

7798; c) J. Penzien, R. Q. Su, T. E. Müller, J. Mol. Catal. 2002, 182–183,<br />

489–498; d) R. Q. Su, T. E. Müller, Tetrahedron 2001, 57, 6027–6033.<br />

[11] F. Pohlki, A. S. Heutling, I. Bytschkov, T. Hotopp, S. Doye, Synlett 2002,<br />

799–801.<br />

[12] Y. Shi, J. T. Ciszewski, A. L. Odom, Organometallics 2001, 20, 3967–3969.<br />

[13] V. Khedkar, A. Tillack, M. Beller, Org. Lett. 2003, 5, 4767–4770.<br />

[14] For a recent review on Markovnikov <strong>and</strong> anti-Markovnikov <strong>functionalization</strong><br />

<strong>of</strong> olefins <strong>and</strong> alkynes, see: M. Beller, J. Seayad, A. Tillack, H. Jiao,<br />

Angew. Chem. 2004, 116, 3448–3479; Angew. Chem. Int. Ed. 2004, 43,<br />

3368–3398.<br />

[15] A. Heutling, F. Pohlki, I. Bytschkov, S. Doye, Angew. Chem. 2005, 117,<br />

3011–3013; Angew. Chem. Int. Ed. 2005, 44, 2951–2954.<br />

[16] R. Apodaca, W. Xiao, Org. Lett. 2001, 3, 1745–1748.<br />

[17] L. T. Kaspar, B. Fingerhut, L. Ackermann, Angew. Chem. 2005, 117, 6126–<br />

6128; Angew. Chem. Int. Ed. 2005, 44, 5972–5974.<br />

[18] A. M. Johns, N. Sakai, A. Riddler, J. F. Hartwig, J. Am. Chem. Soc. 2006,<br />

128, 9306–9307.<br />

[19] A. M. Johns, M. Utsunomiya, C. D. Incarvito, J. F. Hartwig, J. Am. Chem.<br />

Soc. 2006, 128, 1828–1839.<br />

[20] T. Kawakami, T. Sugimoto, I. Shibata, A. Baba, H. Matsuda, N. Sonoda, J.<br />

Org. Chem. 1995, 60, 2677–2682.<br />

Received: December 14, 2007<br />

Published online on March 12, 2008<br />

M. Beller et al.<br />

338 www.chemsuschem.org 2008 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim ChemSusChem 2008, 1, 333 – 338

Hooray! Your file is uploaded and ready to be published.

Saved successfully!

Ooh no, something went wrong!