Photodesulfonylation of indoles initiated by electron transfer from triethylamine

Tetrahedron Letters

Volumn 47, Issue 14, 2006, Pages 2409-2412

  Hong, Xuechuan ^a   Mejía Oneto, José M ^a   France, Stefan ^a   Padwa, Albert ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE; TRIETHYLAMINE;

ARTICLE; CHEMICAL REACTION; DEPROTECTION REACTION; ELECTRON TRANSPORT; LIGHT; PHOTOLYSIS;

EID: 33644835178     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.01.152     Document Type: Article

References (53)

1. T.-S. Kam, and Y.-M. Choo Tetrahedron Lett. 44 2003 1317
2. T.S. Kam, and Y.M. Choo Phytochemistry 65 2004 2119
3. T.S. Kam, and Y.M. Choo Helv. Chim. Acta 87 2004 991
4. A. Padwa, S.P. Carter, and H. Nimmesgern J. Org. Chem. 51 1986 1157
5. A. Padwa, S.P. Carter, H. Nimmesgern, and P.D. Stull J. Am. Chem. Soc. 110 1988 2894
6. A. Padwa, G.E. Fryxell, and L. Zhi J. Org. Chem. 53 1988 2875
7. A. Padwa, G.E. Fryxell, and L. Zhi J. Am. Chem. Soc. 112 1990 3100
8. A. Padwa, and S.F. Hornbuckle Chem. Rev. 91 1991 263
9. A. Padwa, and M.D. Weingarten Chem. Rev. 96 1996 223
10. A. Padwa Top. Curr. Chem. 189 1997 121
11. A. Padwa Helv. Chim. Acta 88 2005 1357
12. A. Padwa, V.P. Sandanayaka, and E.A. Curtis J. Am. Chem. Soc. 116 1994 2667
13. A. Padwa, E.A. Curtis, and V.P. Sandanayaka J. Org. Chem. 61 1996 73
14. A. Padwa, and A.T. Price J. Org. Chem. 60 1995 6258
15. A. Padwa, and A.T. Price J. Org. Chem. 63 1998 556
16. J.M. Mejia-Oneto, and A. Padwa Tetrahedron Lett. 45 2004 9115
17. J.M. Mejia-Oneto, and A. Padwa Org. Lett. 6 2004 3241
18. A. Padwa, J. Boonsombat, P. Rashatasakhon, and J. Willis Org. Lett. 7 2005 3725
19. A. Padwa, S.M. Lynch, J.M. Mejia-Oneto, and H. Zhang J. Org. Chem. 70 2005 2206
20. J. Cossy, P. Aclinou, V. Bellosta, N. Furet, J. Baranne-Lafont, D. Sparfel, and C. Souchaud Tetrahedron Lett. 32 1991 1315
21. J. Cossy, J.-L. Ranaivosata, V. Bellosta, J. Ancerewicz, R. Ferritto, and P. Vogel J. Org. Chem. 60 1995 8351
22. J. Cossy, J.-L. Ranaivosata, and V. Bellosta Tetrahedron Lett. 36 1995 2067
23. S.G. Cauwberghs, and P.J. De Clercq Tetrahedron Lett. 29 1988 6501
24. J. De Schrijver, and P.J. De Clerq Tetrahedron Lett. 34 1993 4369
25. A. Padwa, V.P. Sandanayaka, and E.A. Curtis J. Am. Chem. Soc. 116 1994 2667
26. G.W. Gribble, G.L. Fletcher, D. Ketcha, and M. Rajopadhye J. Org. Chem. 54 1989 3264
27. J.E. Saxton Nat. Prod. Rep. 10 1993 349
28. V. du Vigneaud, and O.K. Behrens J. Biol. Chem. 117 1937 27
29. S. Ji, L.B. Gortler, A. Waring, A. Battisti, S. Bank, W.D. Closson, and P. Wriede J. Am. Chem. Soc. 89 1967 5311
30. K.S. Quall, S. Ji, Y.M. Kim, W.D. Closson, and J.A. Zubieta J. Org. Chem. 43 1978 1311
31. H.R. Snyder, and R.E. Heckert J. Am. Chem. Soc. 74 1952 2006
32. C.M. Haskins, and D.W. Knight Tetrahedron Lett. 45 2004 599
33. I. Fleming, J. Frackenpohl, and H. Ila J. Chem. Soc., Perkin Trans. 1 1998 1229
34. G. Sabitha, S. Abraham, B.V. Subba Reddy, and J.S. Yadav Synlett. 1999 1745
35. B. Witulski, and C. Alayrac Angew. Chem., Int. Ed. 41 2002 3281
36. E.J. Gilbert, J.D. Chisholm, and D.L. Van Vranken J. Org. Chem. 64 1999 5670
37. N.K. Garg, R. Sarpong, and B.M. Stoltz J. Am. Chem. Soc. 124 2002 13179
38. E. Vedejs, and S. Lin J. Org. Chem. 59 1994 1602
39. R.C. Roemmele, and H. Rappoport J. Org. Chem. 53 1988 2367
40. H.S. Knowles, A.F. Parsons, R.M. Pettifer, and S. Rickling Tetrahedron 56 2000 979
41. B. Nyasse, L. Grehn, and Y. Ragnarsson Chem. Commun. 1997 1017
42. A. Yasuhara, and T. Sakamoto Tetrahedron Lett. 39 1998 595
43. G. Sabitha, B.V.S. Reddy, S. Abraham, and J.S. Yadav Tetrahedron Lett. 40 1999 1569
44. T. Hamada, A. Nishida, and D. Yonemitsu J. Am. Chem. Soc. 108 1986 140
45. B. Nyasse, L. Grehn, H.L.S. Maia, L.S. Monteiro, and U. Ragnarsson J. Org. Chem. 64 1999 7135
46. C. Li, and P.L. Fuchs Tetrahedron Lett. 34 1993 1855
47. J.F. Art, J.P. Kestemont, and J.P. Soumillion Tetrahedron Lett. 32 1991 1425
48. J.A. Pincock, and A. Jurgens Tetrahedron Lett. 20 1979 1029
49. Q. Liu, Z. Liu, Y.-L. Zhou, W. Zhang, L. Yang, Z.-L. Liu, and W. Yu Synlett 2005 2510
50. D. Belotti, J. Cossy, J.-P. Pete, and C. Portella J. Org. Chem. 51 1986 4196 and references cited therein
51. S.G. Cohen, A. Parola, and G.H. Parsons Jr. Chem. Rev. 73 1973 141
52. M. Mella, M. Fagnoni, M. Freccero, E. Fasani, and A. Albini Chem. Soc. Rev. 27 1998 81
53. 3SnH.