Radical cyclisation reactions with indoles

Tetrahedron Letters

Volumn 44, Issue 9, 2003, Pages 1795-1798

  Flanagan, Stuart R ^a   Harrowven, David C ^a   Bradley, Mark ^a  

^a UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGEN; INDOLE DERIVATIVE; TIN DERIVATIVE; TRIBUTYLTIN HYDRIDE; UNCLASSIFIED DRUG;

ARTICLE; ATOM; CHEMICAL BOND; CYCLIZATION; ELIMINATION REACTION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0037463517     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00094-7     Document Type: Article

References (30)

1. For recent overviews see: (a) Studer, A.; Bossart, M. Tetrahedron 2001, 57, 9649-9667; (b) Aldabbagh, F.; Bowman, W. R. Contemp. Org. Synth. 1997, 4, 261-280; (c) Bowman, W. R.; Cloonan, M. O.; Krintel, S. L. J. Chem. Soc., Perkin Trans. 1 2001, 2885-2902.
2. For recent overviews see: (a) Studer, A.; Bossart, M. Tetrahedron 2001, 57, 9649-9667; (b) Aldabbagh, F.; Bowman, W. R. Contemp. Org. Synth. 1997, 4, 261-280; (c) Bowman, W. R.; Cloonan, M. O.; Krintel, S. L. J. Chem. Soc., Perkin Trans. 1 2001, 2885-2902.
3. For recent overviews see: (a) Studer, A.; Bossart, M. Tetrahedron 2001, 57, 9649-9667; (b) Aldabbagh, F.; Bowman, W. R. Contemp. Org. Synth. 1997, 4, 261-280; (c) Bowman, W. R.; Cloonan, M. O.; Krintel, S. L. J. Chem. Soc., Perkin Trans. 1 2001, 2885-2902.
4. For some recent examples of tributyltin hydride mediated radical cyclisation reactions proceeding by a non-reducing pathway see: (a) Harrowven, D. C.; Nunn, M. I. T.; Fenwick, D. R. Tetrahedron Lett. 2002, 43, 7345-7347; (b) Harrowven, D. C.; Nunn, M. I. T.; Fenwick, D. R. Tetrahedron Lett. 2002, 43, 3189-3191; (c) Harrowven, D. C.; Nunn, M. I. T.; Fenwick, D. R. Tetrahedron Lett. 2002, 43, 3185-3187; (d) Harrowven, D. C.; Sutton, B. J.; Coulton, S. Tetrahedron 2002, 58, 3387-3400; (e) Nunez, A.; de Viedma, A. G.; Martinez-Barrasa, V.; Burgos, C.; Alvarez-Builla, J. Synlett 2002, 1093-1096; (f) Bowman, W. R.; Bridge, C. F.; Brookes, P.; Cloonan, M. O.; Leach, D. C. J. Chem. Soc., Perkin Trans. 1 2002, 58-68; (g) Harrowven, D. C.; Nunn, M. I. T.; Blumire, N. J.; Fenwick, D. R. Tetrahedron 2001, 57, 4447-4454; (h) Allin, S. M.; Barton, W. R. S.; Bowman, W. R.; McInally, T. Tetrahedron Lett. 2001, 42, 7887-7890; (i) Bowman, W. R.; Mann, E.; Parr, J. J. Chem. Soc., Perkin Trans. 1, 2000, 2991-2999.
5. For some recent examples of tributyltin hydride mediated radical cyclisation reactions proceeding by a non-reducing pathway see: (a) Harrowven, D. C.; Nunn, M. I. T.; Fenwick, D. R. Tetrahedron Lett. 2002, 43, 7345-7347; (b) Harrowven, D. C.; Nunn, M. I. T.; Fenwick, D. R. Tetrahedron Lett. 2002, 43, 3189-3191; (c) Harrowven, D. C.; Nunn, M. I. T.; Fenwick, D. R. Tetrahedron Lett. 2002, 43, 3185-3187; (d) Harrowven, D. C.; Sutton, B. J.; Coulton, S. Tetrahedron 2002, 58, 3387-3400; (e) Nunez, A.; de Viedma, A. G.; Martinez-Barrasa, V.; Burgos, C.; Alvarez-Builla, J. Synlett 2002, 1093-1096; (f) Bowman, W. R.; Bridge, C. F.; Brookes, P.; Cloonan, M. O.; Leach, D. C. J. Chem. Soc., Perkin Trans. 1 2002, 58-68; (g) Harrowven, D. C.; Nunn, M. I. T.; Blumire, N. J.; Fenwick, D. R. Tetrahedron 2001, 57, 4447-4454; (h) Allin, S. M.; Barton, W. R. S.; Bowman, W. R.; McInally, T. Tetrahedron Lett. 2001, 42, 7887-7890; (i) Bowman, W. R.; Mann, E.; Parr, J. J. Chem. Soc., Perkin Trans. 1, 2000, 2991-2999.
6. For some recent examples of tributyltin hydride mediated radical cyclisation reactions proceeding by a non-reducing pathway see: (a) Harrowven, D. C.; Nunn, M. I. T.; Fenwick, D. R. Tetrahedron Lett. 2002, 43, 7345-7347; (b) Harrowven, D. C.; Nunn, M. I. T.; Fenwick, D. R. Tetrahedron Lett. 2002, 43, 3189-3191; (c) Harrowven, D. C.; Nunn, M. I. T.; Fenwick, D. R. Tetrahedron Lett. 2002, 43, 3185-3187; (d) Harrowven, D. C.; Sutton, B. J.; Coulton, S. Tetrahedron 2002, 58, 3387-3400; (e) Nunez, A.; de Viedma, A. G.; Martinez-Barrasa, V.; Burgos, C.; Alvarez-Builla, J. Synlett 2002, 1093-1096; (f) Bowman, W. R.; Bridge, C. F.; Brookes, P.; Cloonan, M. O.; Leach, D. C. J. Chem. Soc., Perkin Trans. 1 2002, 58-68; (g) Harrowven, D. C.; Nunn, M. I. T.; Blumire, N. J.; Fenwick, D. R. Tetrahedron 2001, 57, 4447-4454; (h) Allin, S. M.; Barton, W. R. S.; Bowman, W. R.; McInally, T. Tetrahedron Lett. 2001, 42, 7887-7890; (i) Bowman, W. R.; Mann, E.; Parr, J. J. Chem. Soc., Perkin Trans. 1, 2000, 2991-2999.
7. For some recent examples of tributyltin hydride mediated radical cyclisation reactions proceeding by a non-reducing pathway see: (a) Harrowven, D. C.; Nunn, M. I. T.; Fenwick, D. R. Tetrahedron Lett. 2002, 43, 7345-7347; (b) Harrowven, D. C.; Nunn, M. I. T.; Fenwick, D. R. Tetrahedron Lett. 2002, 43, 3189-3191; (c) Harrowven, D. C.; Nunn, M. I. T.; Fenwick, D. R. Tetrahedron Lett. 2002, 43, 3185-3187; (d) Harrowven, D. C.; Sutton, B. J.; Coulton, S. Tetrahedron 2002, 58, 3387-3400; (e) Nunez, A.; de Viedma, A. G.; Martinez-Barrasa, V.; Burgos, C.; Alvarez-Builla, J. Synlett 2002, 1093-1096; (f) Bowman, W. R.; Bridge, C. F.; Brookes, P.; Cloonan, M. O.; Leach, D. C. J. Chem. Soc., Perkin Trans. 1 2002, 58-68; (g) Harrowven, D. C.; Nunn, M. I. T.; Blumire, N. J.; Fenwick, D. R. Tetrahedron 2001, 57, 4447-4454; (h) Allin, S. M.; Barton, W. R. S.; Bowman, W. R.; McInally, T. Tetrahedron Lett. 2001, 42, 7887-7890; (i) Bowman, W. R.; Mann, E.; Parr, J. J. Chem. Soc., Perkin Trans. 1, 2000, 2991-2999.
8. For some recent examples of tributyltin hydride mediated radical cyclisation reactions proceeding by a non-reducing pathway see: (a) Harrowven, D. C.; Nunn, M. I. T.; Fenwick, D. R. Tetrahedron Lett. 2002, 43, 7345-7347; (b) Harrowven, D. C.; Nunn, M. I. T.; Fenwick, D. R. Tetrahedron Lett. 2002, 43, 3189-3191; (c) Harrowven, D. C.; Nunn, M. I. T.; Fenwick, D. R. Tetrahedron Lett. 2002, 43, 3185-3187; (d) Harrowven, D. C.; Sutton, B. J.; Coulton, S. Tetrahedron 2002, 58, 3387-3400; (e) Nunez, A.; de Viedma, A. G.; Martinez-Barrasa, V.; Burgos, C.; Alvarez-Builla, J. Synlett 2002, 1093-1096; (f) Bowman, W. R.; Bridge, C. F.; Brookes, P.; Cloonan, M. O.; Leach, D. C. J. Chem. Soc., Perkin Trans. 1 2002, 58-68; (g) Harrowven, D. C.; Nunn, M. I. T.; Blumire, N. J.; Fenwick, D. R. Tetrahedron 2001, 57, 4447-4454; (h) Allin, S. M.; Barton, W. R. S.; Bowman, W. R.; McInally, T. Tetrahedron Lett. 2001, 42, 7887-7890; (i) Bowman, W. R.; Mann, E.; Parr, J. J. Chem. Soc., Perkin Trans. 1, 2000, 2991-2999.
9. For some recent examples of tributyltin hydride mediated radical cyclisation reactions proceeding by a non-reducing pathway see: (a) Harrowven, D. C.; Nunn, M. I. T.; Fenwick, D. R. Tetrahedron Lett. 2002, 43, 7345-7347; (b) Harrowven, D. C.; Nunn, M. I. T.; Fenwick, D. R. Tetrahedron Lett. 2002, 43, 3189-3191; (c) Harrowven, D. C.; Nunn, M. I. T.; Fenwick, D. R. Tetrahedron Lett. 2002, 43, 3185-3187; (d) Harrowven, D. C.; Sutton, B. J.; Coulton, S. Tetrahedron 2002, 58, 3387-3400; (e) Nunez, A.; de Viedma, A. G.; Martinez-Barrasa, V.; Burgos, C.; Alvarez-Builla, J. Synlett 2002, 1093-1096; (f) Bowman, W. R.; Bridge, C. F.; Brookes, P.; Cloonan, M. O.; Leach, D. C. J. Chem. Soc., Perkin Trans. 1 2002, 58-68; (g) Harrowven, D. C.; Nunn, M. I. T.; Blumire, N. J.; Fenwick, D. R. Tetrahedron 2001, 57, 4447-4454; (h) Allin, S. M.; Barton, W. R. S.; Bowman, W. R.; McInally, T. Tetrahedron Lett. 2001, 42, 7887-7890; (i) Bowman, W. R.; Mann, E.; Parr, J. J. Chem. Soc., Perkin Trans. 1, 2000, 2991-2999.
10. For some recent examples of tributyltin hydride mediated radical cyclisation reactions proceeding by a non-reducing pathway see: (a) Harrowven, D. C.; Nunn, M. I. T.; Fenwick, D. R. Tetrahedron Lett. 2002, 43, 7345-7347; (b) Harrowven, D. C.; Nunn, M. I. T.; Fenwick, D. R. Tetrahedron Lett. 2002, 43, 3189-3191; (c) Harrowven, D. C.; Nunn, M. I. T.; Fenwick, D. R. Tetrahedron Lett. 2002, 43, 3185-3187; (d) Harrowven, D. C.; Sutton, B. J.; Coulton, S. Tetrahedron 2002, 58, 3387-3400; (e) Nunez, A.; de Viedma, A. G.; Martinez-Barrasa, V.; Burgos, C.; Alvarez-Builla, J. Synlett 2002, 1093-1096; (f) Bowman, W. R.; Bridge, C. F.; Brookes, P.; Cloonan, M. O.; Leach, D. C. J. Chem. Soc., Perkin Trans. 1 2002, 58-68; (g) Harrowven, D. C.; Nunn, M. I. T.; Blumire, N. J.; Fenwick, D. R. Tetrahedron 2001, 57, 4447-4454; (h) Allin, S. M.; Barton, W. R. S.; Bowman, W. R.; McInally, T. Tetrahedron Lett. 2001, 42, 7887-7890; (i) Bowman, W. R.; Mann, E.; Parr, J. J. Chem. Soc., Perkin Trans. 1, 2000, 2991-2999.
11. For some recent examples of tributyltin hydride mediated radical cyclisation reactions proceeding by a non-reducing pathway see: (a) Harrowven, D. C.; Nunn, M. I. T.; Fenwick, D. R. Tetrahedron Lett. 2002, 43, 7345-7347; (b) Harrowven, D. C.; Nunn, M. I. T.; Fenwick, D. R. Tetrahedron Lett. 2002, 43, 3189-3191; (c) Harrowven, D. C.; Nunn, M. I. T.; Fenwick, D. R. Tetrahedron Lett. 2002, 43, 3185-3187; (d) Harrowven, D. C.; Sutton, B. J.; Coulton, S. Tetrahedron 2002, 58, 3387-3400; (e) Nunez, A.; de Viedma, A. G.; Martinez-Barrasa, V.; Burgos, C.; Alvarez-Builla, J. Synlett 2002, 1093-1096; (f) Bowman, W. R.; Bridge, C. F.; Brookes, P.; Cloonan, M. O.; Leach, D. C. J. Chem. Soc., Perkin Trans. 1 2002, 58-68; (g) Harrowven, D. C.; Nunn, M. I. T.; Blumire, N. J.; Fenwick, D. R. Tetrahedron 2001, 57, 4447-4454; (h) Allin, S. M.; Barton, W. R. S.; Bowman, W. R.; McInally, T. Tetrahedron Lett. 2001, 42, 7887-7890; (i) Bowman, W. R.; Mann, E.; Parr, J. J. Chem. Soc., Perkin Trans. 1, 2000, 2991-2999.
12. For some recent examples of tributyltin hydride mediated radical cyclisation reactions proceeding by a non-reducing pathway see: (a) Harrowven, D. C.; Nunn, M. I. T.; Fenwick, D. R. Tetrahedron Lett. 2002, 43, 7345-7347; (b) Harrowven, D. C.; Nunn, M. I. T.; Fenwick, D. R. Tetrahedron Lett. 2002, 43, 3189-3191; (c) Harrowven, D. C.; Nunn, M. I. T.; Fenwick, D. R. Tetrahedron Lett. 2002, 43, 3185-3187; (d) Harrowven, D. C.; Sutton, B. J.; Coulton, S. Tetrahedron 2002, 58, 3387-3400; (e) Nunez, A.; de Viedma, A. G.; Martinez-Barrasa, V.; Burgos, C.; Alvarez-Builla, J. Synlett 2002, 1093-1096; (f) Bowman, W. R.; Bridge, C. F.; Brookes, P.; Cloonan, M. O.; Leach, D. C. J. Chem. Soc., Perkin Trans. 1 2002, 58-68; (g) Harrowven, D. C.; Nunn, M. I. T.; Blumire, N. J.; Fenwick, D. R. Tetrahedron 2001, 57, 4447-4454; (h) Allin, S. M.; Barton, W. R. S.; Bowman, W. R.; McInally, T. Tetrahedron Lett. 2001, 42, 7887-7890; (i) Bowman, W. R.; Mann, E.; Parr, J. J. Chem. Soc., Perkin Trans. 1, 2000, 2991-2999.
13. For examples of radical additions to an indole see (a) Gribble, G. W.; Fraser, H. L.; Badenock, J. C. J. Chem. Soc., Chem. Commun. 2001, 805-806; (b) Miranda, L. D.; Cruz-Almanza, R.; Pavón, M.; Romero, Y.; Muchowski, J. M. Tetrahedron Lett. 2000, 41, 10181-10184; (c) Zhang, W.; Pugh, G. Tetrahedron Lett. 1999, 40, 7591-7594; (d) Wang, S.-F.; Chuang, C.-P.; Lee, W.-H. Tetrahedron 1999, 55, 6109-6118; (e) Tsuge, O.; Hatta, T.; Tsuchiyama, H. Chem. Lett. 1998, 155-156; (f) Ziegler, F. E.; Belema, M. J. Org. Chem. 1997, 62, 1083-1094; (g) Moody, C. J.; Norton, C. L. J. Chem. Soc., Perkin Trans. 1 1997, 2639-2643; (h) Caddick, S.; Aboutayab, K.; Jenkins, K.; West, R. I. J. Chem. Soc., Perkin Trans. 1 1996, 675-682; (i) Kraus, G. A.; Kim, H. Synth. Commun. 1993, 23, 55-64; (j) Yang, C.-C.; Chang, H.-T.; Fang, J.-M. J. Org. Chem. 1993, 58, 3100-3105; (k) Bennasar, M.-L.; Roca, T.; Griera, R.; Bosch, J. J. Org. Chem. 2001, 66, 7547-7551.
14. For examples of radical additions to an indole see (a) Gribble, G. W.; Fraser, H. L.; Badenock, J. C. J. Chem. Soc., Chem. Commun. 2001, 805-806; (b) Miranda, L. D.; Cruz-Almanza, R.; Pavón, M.; Romero, Y.; Muchowski, J. M. Tetrahedron Lett. 2000, 41, 10181-10184; (c) Zhang, W.; Pugh, G. Tetrahedron Lett. 1999, 40, 7591-7594; (d) Wang, S.-F.; Chuang, C.-P.; Lee, W.-H. Tetrahedron 1999, 55, 6109-6118; (e) Tsuge, O.; Hatta, T.; Tsuchiyama, H. Chem. Lett. 1998, 155-156; (f) Ziegler, F. E.; Belema, M. J. Org. Chem. 1997, 62, 1083-1094; (g) Moody, C. J.; Norton, C. L. J. Chem. Soc., Perkin Trans. 1 1997, 2639-2643; (h) Caddick, S.; Aboutayab, K.; Jenkins, K.; West, R. I. J. Chem. Soc., Perkin Trans. 1 1996, 675-682; (i) Kraus, G. A.; Kim, H. Synth. Commun. 1993, 23, 55-64; (j) Yang, C.-C.; Chang, H.-T.; Fang, J.-M. J. Org. Chem. 1993, 58, 3100-3105; (k) Bennasar, M.-L.; Roca, T.; Griera, R.; Bosch, J. J. Org. Chem. 2001, 66, 7547-7551.
15. For examples of radical additions to an indole see (a) Gribble, G. W.; Fraser, H. L.; Badenock, J. C. J. Chem. Soc., Chem. Commun. 2001, 805-806; (b) Miranda, L. D.; Cruz-Almanza, R.; Pavón, M.; Romero, Y.; Muchowski, J. M. Tetrahedron Lett. 2000, 41, 10181-10184; (c) Zhang, W.; Pugh, G. Tetrahedron Lett. 1999, 40, 7591-7594; (d) Wang, S.-F.; Chuang, C.-P.; Lee, W.-H. Tetrahedron 1999, 55, 6109-6118; (e) Tsuge, O.; Hatta, T.; Tsuchiyama, H. Chem. Lett. 1998, 155-156; (f) Ziegler, F. E.; Belema, M. J. Org. Chem. 1997, 62, 1083-1094; (g) Moody, C. J.; Norton, C. L. J. Chem. Soc., Perkin Trans. 1 1997, 2639-2643; (h) Caddick, S.; Aboutayab, K.; Jenkins, K.; West, R. I. J. Chem. Soc., Perkin Trans. 1 1996, 675-682; (i) Kraus, G. A.; Kim, H. Synth. Commun. 1993, 23, 55-64; (j) Yang, C.-C.; Chang, H.-T.; Fang, J.-M. J. Org. Chem. 1993, 58, 3100-3105; (k) Bennasar, M.-L.; Roca, T.; Griera, R.; Bosch, J. J. Org. Chem. 2001, 66, 7547-7551.
16. For examples of radical additions to an indole see (a) Gribble, G. W.; Fraser, H. L.; Badenock, J. C. J. Chem. Soc., Chem. Commun. 2001, 805-806; (b) Miranda, L. D.; Cruz-Almanza, R.; Pavón, M.; Romero, Y.; Muchowski, J. M. Tetrahedron Lett. 2000, 41, 10181-10184; (c) Zhang, W.; Pugh, G. Tetrahedron Lett. 1999, 40, 7591-7594; (d) Wang, S.-F.; Chuang, C.-P.; Lee, W.-H. Tetrahedron 1999, 55, 6109-6118; (e) Tsuge, O.; Hatta, T.; Tsuchiyama, H. Chem. Lett. 1998, 155-156; (f) Ziegler, F. E.; Belema, M. J. Org. Chem. 1997, 62, 1083-1094; (g) Moody, C. J.; Norton, C. L. J. Chem. Soc., Perkin Trans. 1 1997, 2639-2643; (h) Caddick, S.; Aboutayab, K.; Jenkins, K.; West, R. I. J. Chem. Soc., Perkin Trans. 1 1996, 675-682; (i) Kraus, G. A.; Kim, H. Synth. Commun. 1993, 23, 55-64; (j) Yang, C.-C.; Chang, H.-T.; Fang, J.-M. J. Org. Chem. 1993, 58, 3100-3105; (k) Bennasar, M.-L.; Roca, T.; Griera, R.; Bosch, J. J. Org. Chem. 2001, 66, 7547-7551.
17. For examples of radical additions to an indole see (a) Gribble, G. W.; Fraser, H. L.; Badenock, J. C. J. Chem. Soc., Chem. Commun. 2001, 805-806; (b) Miranda, L. D.; Cruz-Almanza, R.; Pavón, M.; Romero, Y.; Muchowski, J. M. Tetrahedron Lett. 2000, 41, 10181-10184; (c) Zhang, W.; Pugh, G. Tetrahedron Lett. 1999, 40, 7591-7594; (d) Wang, S.-F.; Chuang, C.-P.; Lee, W.-H. Tetrahedron 1999, 55, 6109-6118; (e) Tsuge, O.; Hatta, T.; Tsuchiyama, H. Chem. Lett. 1998, 155-156; (f) Ziegler, F. E.; Belema, M. J. Org. Chem. 1997, 62, 1083-1094; (g) Moody, C. J.; Norton, C. L. J. Chem. Soc., Perkin Trans. 1 1997, 2639-2643; (h) Caddick, S.; Aboutayab, K.; Jenkins, K.; West, R. I. J. Chem. Soc., Perkin Trans. 1 1996, 675-682; (i) Kraus, G. A.; Kim, H. Synth. Commun. 1993, 23, 55-64; (j) Yang, C.-C.; Chang, H.-T.; Fang, J.-M. J. Org. Chem. 1993, 58, 3100-3105; (k) Bennasar, M.-L.; Roca, T.; Griera, R.; Bosch, J. J. Org. Chem. 2001, 66, 7547-7551.
18. For examples of radical additions to an indole see (a) Gribble, G. W.; Fraser, H. L.; Badenock, J. C. J. Chem. Soc., Chem. Commun. 2001, 805-806; (b) Miranda, L. D.; Cruz-Almanza, R.; Pavón, M.; Romero, Y.; Muchowski, J. M. Tetrahedron Lett. 2000, 41, 10181-10184; (c) Zhang, W.; Pugh, G. Tetrahedron Lett. 1999, 40, 7591-7594; (d) Wang, S.-F.; Chuang, C.-P.; Lee, W.-H. Tetrahedron 1999, 55, 6109-6118; (e) Tsuge, O.; Hatta, T.; Tsuchiyama, H. Chem. Lett. 1998, 155-156; (f) Ziegler, F. E.; Belema, M. J. Org. Chem. 1997, 62, 1083-1094; (g) Moody, C. J.; Norton, C. L. J. Chem. Soc., Perkin Trans. 1 1997, 2639-2643; (h) Caddick, S.; Aboutayab, K.; Jenkins, K.; West, R. I. J. Chem. Soc., Perkin Trans. 1 1996, 675-682; (i) Kraus, G. A.; Kim, H. Synth. Commun. 1993, 23, 55-64; (j) Yang, C.-C.; Chang, H.-T.; Fang, J.-M. J. Org. Chem. 1993, 58, 3100-3105; (k) Bennasar, M.-L.; Roca, T.; Griera, R.; Bosch, J. J. Org. Chem. 2001, 66, 7547-7551.
19. For examples of radical additions to an indole see (a) Gribble, G. W.; Fraser, H. L.; Badenock, J. C. J. Chem. Soc., Chem. Commun. 2001, 805-806; (b) Miranda, L. D.; Cruz-Almanza, R.; Pavón, M.; Romero, Y.; Muchowski, J. M. Tetrahedron Lett. 2000, 41, 10181-10184; (c) Zhang, W.; Pugh, G. Tetrahedron Lett. 1999, 40, 7591-7594; (d) Wang, S.-F.; Chuang, C.-P.; Lee, W.-H. Tetrahedron 1999, 55, 6109-6118; (e) Tsuge, O.; Hatta, T.; Tsuchiyama, H. Chem. Lett. 1998, 155-156; (f) Ziegler, F. E.; Belema, M. J. Org. Chem. 1997, 62, 1083-1094; (g) Moody, C. J.; Norton, C. L. J. Chem. Soc., Perkin Trans. 1 1997, 2639-2643; (h) Caddick, S.; Aboutayab, K.; Jenkins, K.; West, R. I. J. Chem. Soc., Perkin Trans. 1 1996, 675-682; (i) Kraus, G. A.; Kim, H. Synth. Commun. 1993, 23, 55-64; (j) Yang, C.-C.; Chang, H.-T.; Fang, J.-M. J. Org. Chem. 1993, 58, 3100-3105; (k) Bennasar, M.-L.; Roca, T.; Griera, R.; Bosch, J. J. Org. Chem. 2001, 66, 7547-7551.
20. For examples of radical additions to an indole see (a) Gribble, G. W.; Fraser, H. L.; Badenock, J. C. J. Chem. Soc., Chem. Commun. 2001, 805-806; (b) Miranda, L. D.; Cruz-Almanza, R.; Pavón, M.; Romero, Y.; Muchowski, J. M. Tetrahedron Lett. 2000, 41, 10181-10184; (c) Zhang, W.; Pugh, G. Tetrahedron Lett. 1999, 40, 7591-7594; (d) Wang, S.-F.; Chuang, C.-P.; Lee, W.-H. Tetrahedron 1999, 55, 6109-6118; (e) Tsuge, O.; Hatta, T.; Tsuchiyama, H. Chem. Lett. 1998, 155-156; (f) Ziegler, F. E.; Belema, M. J. Org. Chem. 1997, 62, 1083-1094; (g) Moody, C. J.; Norton, C. L. J. Chem. Soc., Perkin Trans. 1 1997, 2639-2643; (h) Caddick, S.; Aboutayab, K.; Jenkins, K.; West, R. I. J. Chem. Soc., Perkin Trans. 1 1996, 675-682; (i) Kraus, G. A.; Kim, H. Synth. Commun. 1993, 23, 55-64; (j) Yang, C.-C.; Chang, H.-T.; Fang, J.-M. J. Org. Chem. 1993, 58, 3100-3105; (k) Bennasar, M.-L.; Roca, T.; Griera, R.; Bosch, J. J. Org. Chem. 2001, 66, 7547-7551.
21. For examples of radical additions to an indole see (a) Gribble, G. W.; Fraser, H. L.; Badenock, J. C. J. Chem. Soc., Chem. Commun. 2001, 805-806; (b) Miranda, L. D.; Cruz-Almanza, R.; Pavón, M.; Romero, Y.; Muchowski, J. M. Tetrahedron Lett. 2000, 41, 10181-10184; (c) Zhang, W.; Pugh, G. Tetrahedron Lett. 1999, 40, 7591-7594; (d) Wang, S.-F.; Chuang, C.-P.; Lee, W.-H. Tetrahedron 1999, 55, 6109-6118; (e) Tsuge, O.; Hatta, T.; Tsuchiyama, H. Chem. Lett. 1998, 155-156; (f) Ziegler, F. E.; Belema, M. J. Org. Chem. 1997, 62, 1083-1094; (g) Moody, C. J.; Norton, C. L. J. Chem. Soc., Perkin Trans. 1 1997, 2639-2643; (h) Caddick, S.; Aboutayab, K.; Jenkins, K.; West, R. I. J. Chem. Soc., Perkin Trans. 1 1996, 675-682; (i) Kraus, G. A.; Kim, H. Synth. Commun. 1993, 23, 55-64; (j) Yang, C.-C.; Chang, H.-T.; Fang, J.-M. J. Org. Chem. 1993, 58, 3100-3105; (k) Bennasar, M.-L.; Roca, T.; Griera, R.; Bosch, J. J. Org. Chem. 2001, 66, 7547-7551.
22. For examples of radical additions to an indole see (a) Gribble, G. W.; Fraser, H. L.; Badenock, J. C. J. Chem. Soc., Chem. Commun. 2001, 805-806; (b) Miranda, L. D.; Cruz-Almanza, R.; Pavón, M.; Romero, Y.; Muchowski, J. M. Tetrahedron Lett. 2000, 41, 10181-10184; (c) Zhang, W.; Pugh, G. Tetrahedron Lett. 1999, 40, 7591-7594; (d) Wang, S.-F.; Chuang, C.-P.; Lee, W.-H. Tetrahedron 1999, 55, 6109-6118; (e) Tsuge, O.; Hatta, T.; Tsuchiyama, H. Chem. Lett. 1998, 155-156; (f) Ziegler, F. E.; Belema, M. J. Org. Chem. 1997, 62, 1083-1094; (g) Moody, C. J.; Norton, C. L. J. Chem. Soc., Perkin Trans. 1 1997, 2639-2643; (h) Caddick, S.; Aboutayab, K.; Jenkins, K.; West, R. I. J. Chem. Soc., Perkin Trans. 1 1996, 675-682; (i) Kraus, G. A.; Kim, H. Synth. Commun. 1993, 23, 55-64; (j) Yang, C.-C.; Chang, H.-T.; Fang, J.-M. J. Org. Chem. 1993, 58, 3100-3105; (k) Bennasar, M.-L.; Roca, T.; Griera, R.; Bosch, J. J. Org. Chem. 2001, 66, 7547-7551.
23. For examples of radical additions to an indole see (a) Gribble, G. W.; Fraser, H. L.; Badenock, J. C. J. Chem. Soc., Chem. Commun. 2001, 805-806; (b) Miranda, L. D.; Cruz-Almanza, R.; Pavón, M.; Romero, Y.; Muchowski, J. M. Tetrahedron Lett. 2000, 41, 10181-10184; (c) Zhang, W.; Pugh, G. Tetrahedron Lett. 1999, 40, 7591-7594; (d) Wang, S.-F.; Chuang, C.-P.; Lee, W.-H. Tetrahedron 1999, 55, 6109-6118; (e) Tsuge, O.; Hatta, T.; Tsuchiyama, H. Chem. Lett. 1998, 155-156; (f) Ziegler, F. E.; Belema, M. J. Org. Chem. 1997, 62, 1083-1094; (g) Moody, C. J.; Norton, C. L. J. Chem. Soc., Perkin Trans. 1 1997, 2639-2643; (h) Caddick, S.; Aboutayab, K.; Jenkins, K.; West, R. I. J. Chem. Soc., Perkin Trans. 1 1996, 675-682; (i) Kraus, G. A.; Kim, H. Synth. Commun. 1993, 23, 55-64; (j) Yang, C.-C.; Chang, H.-T.; Fang, J.-M. J. Org. Chem. 1993, 58, 3100-3105; (k) Bennasar, M.-L.; Roca, T.; Griera, R.; Bosch, J. J. Org. Chem. 2001, 66, 7547-7551.
24. Smith T.W., Butler G.B. J. Org. Chem. 43:1978;6-13.
25. Harrowven D.C., Sutton B.J., Coulton S. Tetrahedron Lett. 42:2001;9061-9064.
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28. For Table entries a-c, recovered starting material accounted for 15-20% of the mass balance.
29. Mohanakrishnan A.K., Srinivasan P.C. Tetrahedron Lett. 37:1996;2659-2662.
30. Sundberg R.J., Cherney R.J. J. Org. Chem. 55:1990;6028-6037.