Selective functionalization in positions 2 and 3 of indole via an iodine - Copper exchange reaction

Organic Letters

Volumn 6, Issue 10, 2004, Pages 1665-1667

  Yang, Xiaoyin ^a   Althammer, Andreas ^a   Knochel, Paul ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2,3 DIKETONE DERIVATIVE; COPPER COMPLEX; HETEROCYCLIC COMPOUND; INDOLE; IODINE DERIVATIVE; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; METHODOLOGY;

EID: 2542569632     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049498q     Document Type: Article

References (35)

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2. For some recent methods, see: (a) Gribble, G. W. J. Chem. Soc., Perkin Trans 1. 2000, 1045-1048. (b) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem. 2002, 2671-2681. (c) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Marinelli, F.; Parisi, L. M. Org. Lett. 2002, 4, 1355-1358. (d) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-704. (e) Beller, M.; Breinde, C.; Riermeier, T. H.; Eichberger, M; Tranlhwein, H Angew. Chem., Int. Ed. 1998, 37, 3389-3391. (f) Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1999, 38, 2426-2430. (g) Kondo, Y.; Kojima, S.; Sakamoto, T. J. Org. Chem. 1997, 62, 6507-6511. (h) Coleman, R. S.; Chen, W. Org. Lett. 2001, 3, 1141-1144. (i) Watanabe, M.; Yamamoto, T.; Nishiyama, M. Angew. Chem., Int. Ed. 2000, 39, 2501-2504. (j) Takeda, A.; Kamijo, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 5662-5663. (k) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251-10263. (l) Koradin, C.; Dohle, W.; Rodriguez, A. L.; Schmid, B.; Knochel, P. Tetrahedron 2003, 59, 1571-1578. (m) Köhling, P.; Schmidt, A. M.; Eilbracht, P. Org. Lett. 2003, 5, 3213-3216. (n) Knepper, K.; Bräse, S. Org. Lett. 2003, 5, 2829-2832. (o) Barluenga, J. Pure Appl. Chem. 2002, 74, 1317-1326.
3. For some recent methods, see: (a) Gribble, G. W. J. Chem. Soc., Perkin Trans 1. 2000, 1045-1048. (b) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem. 2002, 2671-2681. (c) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Marinelli, F.; Parisi, L. M. Org. Lett. 2002, 4, 1355-1358. (d) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-704. (e) Beller, M.; Breinde, C.; Riermeier, T. H.; Eichberger, M; Tranlhwein, H Angew. Chem., Int. Ed. 1998, 37, 3389-3391. (f) Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1999, 38, 2426-2430. (g) Kondo, Y.; Kojima, S.; Sakamoto, T. J. Org. Chem. 1997, 62, 6507-6511. (h) Coleman, R. S.; Chen, W. Org. Lett. 2001, 3, 1141-1144. (i) Watanabe, M.; Yamamoto, T.; Nishiyama, M. Angew. Chem., Int. Ed. 2000, 39, 2501-2504. (j) Takeda, A.; Kamijo, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 5662-5663. (k) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251-10263. (l) Koradin, C.; Dohle, W.; Rodriguez, A. L.; Schmid, B.; Knochel, P. Tetrahedron 2003, 59, 1571-1578. (m) Köhling, P.; Schmidt, A. M.; Eilbracht, P. Org. Lett. 2003, 5, 3213-3216. (n) Knepper, K.; Bräse, S. Org. Lett. 2003, 5, 2829-2832. (o) Barluenga, J. Pure Appl. Chem. 2002, 74, 1317-1326.
4. For some recent methods, see: (a) Gribble, G. W. J. Chem. Soc., Perkin Trans 1. 2000, 1045-1048. (b) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem. 2002, 2671-2681. (c) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Marinelli, F.; Parisi, L. M. Org. Lett. 2002, 4, 1355-1358. (d) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-704. (e) Beller, M.; Breinde, C.; Riermeier, T. H.; Eichberger, M; Tranlhwein, H Angew. Chem., Int. Ed. 1998, 37, 3389-3391. (f) Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1999, 38, 2426-2430. (g) Kondo, Y.; Kojima, S.; Sakamoto, T. J. Org. Chem. 1997, 62, 6507-6511. (h) Coleman, R. S.; Chen, W. Org. Lett. 2001, 3, 1141-1144. (i) Watanabe, M.; Yamamoto, T.; Nishiyama, M. Angew. Chem., Int. Ed. 2000, 39, 2501-2504. (j) Takeda, A.; Kamijo, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 5662-5663. (k) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251-10263. (l) Koradin, C.; Dohle, W.; Rodriguez, A. L.; Schmid, B.; Knochel, P. Tetrahedron 2003, 59, 1571-1578. (m) Köhling, P.; Schmidt, A. M.; Eilbracht, P. Org. Lett. 2003, 5, 3213-3216. (n) Knepper, K.; Bräse, S. Org. Lett. 2003, 5, 2829-2832. (o) Barluenga, J. Pure Appl. Chem. 2002, 74, 1317-1326.
5. For some recent methods, see: (a) Gribble, G. W. J. Chem. Soc., Perkin Trans 1. 2000, 1045-1048. (b) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem. 2002, 2671-2681. (c) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Marinelli, F.; Parisi, L. M. Org. Lett. 2002, 4, 1355-1358. (d) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-704. (e) Beller, M.; Breinde, C.; Riermeier, T. H.; Eichberger, M; Tranlhwein, H Angew. Chem., Int. Ed. 1998, 37, 3389-3391. (f) Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1999, 38, 2426-2430. (g) Kondo, Y.; Kojima, S.; Sakamoto, T. J. Org. Chem. 1997, 62, 6507-6511. (h) Coleman, R. S.; Chen, W. Org. Lett. 2001, 3, 1141-1144. (i) Watanabe, M.; Yamamoto, T.; Nishiyama, M. Angew. Chem., Int. Ed. 2000, 39, 2501-2504. (j) Takeda, A.; Kamijo, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 5662-5663. (k) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251-10263. (l) Koradin, C.; Dohle, W.; Rodriguez, A. L.; Schmid, B.; Knochel, P. Tetrahedron 2003, 59, 1571-1578. (m) Köhling, P.; Schmidt, A. M.; Eilbracht, P. Org. Lett. 2003, 5, 3213-3216. (n) Knepper, K.; Bräse, S. Org. Lett. 2003, 5, 2829-2832. (o) Barluenga, J. Pure Appl. Chem. 2002, 74, 1317-1326.
6. For some recent methods, see: (a) Gribble, G. W. J. Chem. Soc., Perkin Trans 1. 2000, 1045-1048. (b) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem. 2002, 2671-2681. (c) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Marinelli, F.; Parisi, L. M. Org. Lett. 2002, 4, 1355-1358. (d) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-704. (e) Beller, M.; Breinde, C.; Riermeier, T. H.; Eichberger, M; Tranlhwein, H Angew. Chem., Int. Ed. 1998, 37, 3389-3391. (f) Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1999, 38, 2426-2430. (g) Kondo, Y.; Kojima, S.; Sakamoto, T. J. Org. Chem. 1997, 62, 6507-6511. (h) Coleman, R. S.; Chen, W. Org. Lett. 2001, 3, 1141-1144. (i) Watanabe, M.; Yamamoto, T.; Nishiyama, M. Angew. Chem., Int. Ed. 2000, 39, 2501-2504. (j) Takeda, A.; Kamijo, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 5662-5663. (k) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251-10263. (l) Koradin, C.; Dohle, W.; Rodriguez, A. L.; Schmid, B.; Knochel, P. Tetrahedron 2003, 59, 1571-1578. (m) Köhling, P.; Schmidt, A. M.; Eilbracht, P. Org. Lett. 2003, 5, 3213-3216. (n) Knepper, K.; Bräse, S. Org. Lett. 2003, 5, 2829-2832. (o) Barluenga, J. Pure Appl. Chem. 2002, 74, 1317-1326.
7. For some recent methods, see: (a) Gribble, G. W. J. Chem. Soc., Perkin Trans 1. 2000, 1045-1048. (b) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem. 2002, 2671-2681. (c) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Marinelli, F.; Parisi, L. M. Org. Lett. 2002, 4, 1355-1358. (d) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-704. (e) Beller, M.; Breinde, C.; Riermeier, T. H.; Eichberger, M; Tranlhwein, H Angew. Chem., Int. Ed. 1998, 37, 3389-3391. (f) Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1999, 38, 2426-2430. (g) Kondo, Y.; Kojima, S.; Sakamoto, T. J. Org. Chem. 1997, 62, 6507-6511. (h) Coleman, R. S.; Chen, W. Org. Lett. 2001, 3, 1141-1144. (i) Watanabe, M.; Yamamoto, T.; Nishiyama, M. Angew. Chem., Int. Ed. 2000, 39, 2501-2504. (j) Takeda, A.; Kamijo, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 5662-5663. (k) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251-10263. (l) Koradin, C.; Dohle, W.; Rodriguez, A. L.; Schmid, B.; Knochel, P. Tetrahedron 2003, 59, 1571-1578. (m) Köhling, P.; Schmidt, A. M.; Eilbracht, P. Org. Lett. 2003, 5, 3213-3216. (n) Knepper, K.; Bräse, S. Org. Lett. 2003, 5, 2829-2832. (o) Barluenga, J. Pure Appl. Chem. 2002, 74, 1317-1326.
8. For some recent methods, see: (a) Gribble, G. W. J. Chem. Soc., Perkin Trans 1. 2000, 1045-1048. (b) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem. 2002, 2671-2681. (c) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Marinelli, F.; Parisi, L. M. Org. Lett. 2002, 4, 1355-1358. (d) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-704. (e) Beller, M.; Breinde, C.; Riermeier, T. H.; Eichberger, M; Tranlhwein, H Angew. Chem., Int. Ed. 1998, 37, 3389-3391. (f) Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1999, 38, 2426-2430. (g) Kondo, Y.; Kojima, S.; Sakamoto, T. J. Org. Chem. 1997, 62, 6507-6511. (h) Coleman, R. S.; Chen, W. Org. Lett. 2001, 3, 1141-1144. (i) Watanabe, M.; Yamamoto, T.; Nishiyama, M. Angew. Chem., Int. Ed. 2000, 39, 2501-2504. (j) Takeda, A.; Kamijo, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 5662-5663. (k) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251-10263. (l) Koradin, C.; Dohle, W.; Rodriguez, A. L.; Schmid, B.; Knochel, P. Tetrahedron 2003, 59, 1571-1578. (m) Köhling, P.; Schmidt, A. M.; Eilbracht, P. Org. Lett. 2003, 5, 3213-3216. (n) Knepper, K.; Bräse, S. Org. Lett. 2003, 5, 2829-2832. (o) Barluenga, J. Pure Appl. Chem. 2002, 74, 1317-1326.
9. For some recent methods, see: (a) Gribble, G. W. J. Chem. Soc., Perkin Trans 1. 2000, 1045-1048. (b) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem. 2002, 2671-2681. (c) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Marinelli, F.; Parisi, L. M. Org. Lett. 2002, 4, 1355-1358. (d) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-704. (e) Beller, M.; Breinde, C.; Riermeier, T. H.; Eichberger, M; Tranlhwein, H Angew. Chem., Int. Ed. 1998, 37, 3389-3391. (f) Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1999, 38, 2426-2430. (g) Kondo, Y.; Kojima, S.; Sakamoto, T. J. Org. Chem. 1997, 62, 6507-6511. (h) Coleman, R. S.; Chen, W. Org. Lett. 2001, 3, 1141-1144. (i) Watanabe, M.; Yamamoto, T.; Nishiyama, M. Angew. Chem., Int. Ed. 2000, 39, 2501-2504. (j) Takeda, A.; Kamijo, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 5662-5663. (k) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251-10263. (l) Koradin, C.; Dohle, W.; Rodriguez, A. L.; Schmid, B.; Knochel, P. Tetrahedron 2003, 59, 1571-1578. (m) Köhling, P.; Schmidt, A. M.; Eilbracht, P. Org. Lett. 2003, 5, 3213-3216. (n) Knepper, K.; Bräse, S. Org. Lett. 2003, 5, 2829-2832. (o) Barluenga, J. Pure Appl. Chem. 2002, 74, 1317-1326.
10. For some recent methods, see: (a) Gribble, G. W. J. Chem. Soc., Perkin Trans 1. 2000, 1045-1048. (b) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem. 2002, 2671-2681. (c) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Marinelli, F.; Parisi, L. M. Org. Lett. 2002, 4, 1355-1358. (d) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-704. (e) Beller, M.; Breinde, C.; Riermeier, T. H.; Eichberger, M; Tranlhwein, H Angew. Chem., Int. Ed. 1998, 37, 3389-3391. (f) Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1999, 38, 2426-2430. (g) Kondo, Y.; Kojima, S.; Sakamoto, T. J. Org. Chem. 1997, 62, 6507-6511. (h) Coleman, R. S.; Chen, W. Org. Lett. 2001, 3, 1141-1144. (i) Watanabe, M.; Yamamoto, T.; Nishiyama, M. Angew. Chem., Int. Ed. 2000, 39, 2501-2504. (j) Takeda, A.; Kamijo, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 5662-5663. (k) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251-10263. (l) Koradin, C.; Dohle, W.; Rodriguez, A. L.; Schmid, B.; Knochel, P. Tetrahedron 2003, 59, 1571-1578. (m) Köhling, P.; Schmidt, A. M.; Eilbracht, P. Org. Lett. 2003, 5, 3213-3216. (n) Knepper, K.; Bräse, S. Org. Lett. 2003, 5, 2829-2832. (o) Barluenga, J. Pure Appl. Chem. 2002, 74, 1317-1326.
11. For some recent methods, see: (a) Gribble, G. W. J. Chem. Soc., Perkin Trans 1. 2000, 1045-1048. (b) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem. 2002, 2671-2681. (c) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Marinelli, F.; Parisi, L. M. Org. Lett. 2002, 4, 1355-1358. (d) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-704. (e) Beller, M.; Breinde, C.; Riermeier, T. H.; Eichberger, M; Tranlhwein, H Angew. Chem., Int. Ed. 1998, 37, 3389-3391. (f) Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1999, 38, 2426-2430. (g) Kondo, Y.; Kojima, S.; Sakamoto, T. J. Org. Chem. 1997, 62, 6507-6511. (h) Coleman, R. S.; Chen, W. Org. Lett. 2001, 3, 1141-1144. (i) Watanabe, M.; Yamamoto, T.; Nishiyama, M. Angew. Chem., Int. Ed. 2000, 39, 2501-2504. (j) Takeda, A.; Kamijo, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 5662-5663. (k) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251-10263. (l) Koradin, C.; Dohle, W.; Rodriguez, A. L.; Schmid, B.; Knochel, P. Tetrahedron 2003, 59, 1571-1578. (m) Köhling, P.; Schmidt, A. M.; Eilbracht, P. Org. Lett. 2003, 5, 3213-3216. (n) Knepper, K.; Bräse, S. Org. Lett. 2003, 5, 2829-2832. (o) Barluenga, J. Pure Appl. Chem. 2002, 74, 1317-1326.
12. For some recent methods, see: (a) Gribble, G. W. J. Chem. Soc., Perkin Trans 1. 2000, 1045-1048. (b) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem. 2002, 2671-2681. (c) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Marinelli, F.; Parisi, L. M. Org. Lett. 2002, 4, 1355-1358. (d) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-704. (e) Beller, M.; Breinde, C.; Riermeier, T. H.; Eichberger, M; Tranlhwein, H Angew. Chem., Int. Ed. 1998, 37, 3389-3391. (f) Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1999, 38, 2426-2430. (g) Kondo, Y.; Kojima, S.; Sakamoto, T. J. Org. Chem. 1997, 62, 6507-6511. (h) Coleman, R. S.; Chen, W. Org. Lett. 2001, 3, 1141-1144. (i) Watanabe, M.; Yamamoto, T.; Nishiyama, M. Angew. Chem., Int. Ed. 2000, 39, 2501-2504. (j) Takeda, A.; Kamijo, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 5662-5663. (k) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251-10263. (l) Koradin, C.; Dohle, W.; Rodriguez, A. L.; Schmid, B.; Knochel, P. Tetrahedron 2003, 59, 1571-1578. (m) Köhling, P.; Schmidt, A. M.; Eilbracht, P. Org. Lett. 2003, 5, 3213-3216. (n) Knepper, K.; Bräse, S. Org. Lett. 2003, 5, 2829-2832. (o) Barluenga, J. Pure Appl. Chem. 2002, 74, 1317-1326.
13. For some recent methods, see: (a) Gribble, G. W. J. Chem. Soc., Perkin Trans 1. 2000, 1045-1048. (b) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem. 2002, 2671-2681. (c) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Marinelli, F.; Parisi, L. M. Org. Lett. 2002, 4, 1355-1358. (d) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-704. (e) Beller, M.; Breinde, C.; Riermeier, T. H.; Eichberger, M; Tranlhwein, H Angew. Chem., Int. Ed. 1998, 37, 3389-3391. (f) Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1999, 38, 2426-2430. (g) Kondo, Y.; Kojima, S.; Sakamoto, T. J. Org. Chem. 1997, 62, 6507-6511. (h) Coleman, R. S.; Chen, W. Org. Lett. 2001, 3, 1141-1144. (i) Watanabe, M.; Yamamoto, T.; Nishiyama, M. Angew. Chem., Int. Ed. 2000, 39, 2501-2504. (j) Takeda, A.; Kamijo, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 5662-5663. (k) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251-10263. (l) Koradin, C.; Dohle, W.; Rodriguez, A. L.; Schmid, B.; Knochel, P. Tetrahedron 2003, 59, 1571-1578. (m) Köhling, P.; Schmidt, A. M.; Eilbracht, P. Org. Lett. 2003, 5, 3213-3216. (n) Knepper, K.; Bräse, S. Org. Lett. 2003, 5, 2829-2832. (o) Barluenga, J. Pure Appl. Chem. 2002, 74, 1317-1326.
14. For some recent methods, see: (a) Gribble, G. W. J. Chem. Soc., Perkin Trans 1. 2000, 1045-1048. (b) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem. 2002, 2671-2681. (c) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Marinelli, F.; Parisi, L. M. Org. Lett. 2002, 4, 1355-1358. (d) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-704. (e) Beller, M.; Breinde, C.; Riermeier, T. H.; Eichberger, M; Tranlhwein, H Angew. Chem., Int. Ed. 1998, 37, 3389-3391. (f) Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1999, 38, 2426-2430. (g) Kondo, Y.; Kojima, S.; Sakamoto, T. J. Org. Chem. 1997, 62, 6507-6511. (h) Coleman, R. S.; Chen, W. Org. Lett. 2001, 3, 1141-1144. (i) Watanabe, M.; Yamamoto, T.; Nishiyama, M. Angew. Chem., Int. Ed. 2000, 39, 2501-2504. (j) Takeda, A.; Kamijo, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 5662-5663. (k) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251-10263. (l) Koradin, C.; Dohle, W.; Rodriguez, A. L.; Schmid, B.; Knochel, P. Tetrahedron 2003, 59, 1571-1578. (m) Köhling, P.; Schmidt, A. M.; Eilbracht, P. Org. Lett. 2003, 5, 3213-3216. (n) Knepper, K.; Bräse, S. Org. Lett. 2003, 5, 2829-2832. (o) Barluenga, J. Pure Appl. Chem. 2002, 74, 1317-1326.
15. For some recent methods, see: (a) Gribble, G. W. J. Chem. Soc., Perkin Trans 1. 2000, 1045-1048. (b) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem. 2002, 2671-2681. (c) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Marinelli, F.; Parisi, L. M. Org. Lett. 2002, 4, 1355-1358. (d) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-704. (e) Beller, M.; Breinde, C.; Riermeier, T. H.; Eichberger, M; Tranlhwein, H Angew. Chem., Int. Ed. 1998, 37, 3389-3391. (f) Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1999, 38, 2426-2430. (g) Kondo, Y.; Kojima, S.; Sakamoto, T. J. Org. Chem. 1997, 62, 6507-6511. (h) Coleman, R. S.; Chen, W. Org. Lett. 2001, 3, 1141-1144. (i) Watanabe, M.; Yamamoto, T.; Nishiyama, M. Angew. Chem., Int. Ed. 2000, 39, 2501-2504. (j) Takeda, A.; Kamijo, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 5662-5663. (k) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251-10263. (l) Koradin, C.; Dohle, W.; Rodriguez, A. L.; Schmid, B.; Knochel, P. Tetrahedron 2003, 59, 1571-1578. (m) Köhling, P.; Schmidt, A. M.; Eilbracht, P. Org. Lett. 2003, 5, 3213-3216. (n) Knepper, K.; Bräse, S. Org. Lett. 2003, 5, 2829-2832. (o) Barluenga, J. Pure Appl. Chem. 2002, 74, 1317-1326.
16. For some recent methods, see: (a) Gribble, G. W. J. Chem. Soc., Perkin Trans 1. 2000, 1045-1048. (b) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem. 2002, 2671-2681. (c) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Marinelli, F.; Parisi, L. M. Org. Lett. 2002, 4, 1355-1358. (d) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-704. (e) Beller, M.; Breinde, C.; Riermeier, T. H.; Eichberger, M; Tranlhwein, H Angew. Chem., Int. Ed. 1998, 37, 3389-3391. (f) Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1999, 38, 2426-2430. (g) Kondo, Y.; Kojima, S.; Sakamoto, T. J. Org. Chem. 1997, 62, 6507-6511. (h) Coleman, R. S.; Chen, W. Org. Lett. 2001, 3, 1141-1144. (i) Watanabe, M.; Yamamoto, T.; Nishiyama, M. Angew. Chem., Int. Ed. 2000, 39, 2501-2504. (j) Takeda, A.; Kamijo, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 5662-5663. (k) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251-10263. (l) Koradin, C.; Dohle, W.; Rodriguez, A. L.; Schmid, B.; Knochel, P. Tetrahedron 2003, 59, 1571-1578. (m) Köhling, P.; Schmidt, A. M.; Eilbracht, P. Org. Lett. 2003, 5, 3213-3216. (n) Knepper, K.; Bräse, S. Org. Lett. 2003, 5, 2829-2832. (o) Barluenga, J. Pure Appl. Chem. 2002, 74, 1317-1326.
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30. 4, and concentrated in vacuo. Purification by flash chromatography yielded 824 mg (86%) of 4c as a white solid, mp 153°C.
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35. 4, and concentrated in vacuo. Purification by flash chromatography yielded 167 mg (73%) of 6c as a white solid, mp 122°C.