Redox chain reaction - Indole and pyrrole alkylation with unactivated secondary alcohols

Angewandte Chemie - International Edition

Volumn 52, Issue 17, 2013, Pages 4637-4640

  Han, Xinping ^a   Wu, Jimmy ^a  

^a Dartmouth College   (United States)

Author keywords

alcohols; alkylation; heterocycles; redox chemistry; synthetic methods

Indexed keywords

ALIPHATIC ALCOHOL; HETEROCYCLES; MECHANISTIC PATHWAYS; PRELIMINARY STUDIES; PYRROLE DERIVATIVES; REDOX CHEMISTRY; SECONDARY ALCOHOLS; SYNTHETIC METHODS;

ALCOHOLS; ALKYLATION; AROMATIC COMPOUNDS; BROMINE COMPOUNDS;

POLYCYCLIC AROMATIC HYDROCARBONS;

EID: 84876479991     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201209810     Document Type: Article

References (48)

1. B. M. Trost, J. Quancard, J. Am. Chem. Soc. 2006, 128, 6314
2. M. Kimura, M. Futamata, R. Mukai, Y. Tamaru, J. Am. Chem. Soc. 2005, 127, 4592
3. I. Usui, S. Schmidt, M. Keller, B. Breit, Org. Lett. 2008, 10, 1207
4. A. B. Zaitsev, S. Gruber, P. A. Plüss, P. S. Pregosin, L. F. Veiros, M. Wörle, J. Am. Chem. Soc. 2008, 130, 11604
5. M. Yasuda, T. Somyo, A. Baba, Angew. Chem. 2006, 118, 807
6. Angew. Chem. Int. Ed. 2006, 45, 793
7. K. J. Henry, Jr., P. A. Grieco, J. Chem. Soc. Chem. Commun. 1993, 510
8. J. S. Yadav, B. V. Reddy, S. Aravind, G. G. K. S. N. Kumar, A. S. Reddy, Tetrahedron Lett. 2007, 48, 6117
9. J. Le Bras, J. Muzart, Tetrahedron 2007, 63, 7942
10. J. S. Yadav, B. V. S. Reddy, P. M. Reddy, C. Srinivas, Tetrahedron Lett. 2002, 43, 5185
11. D. Prajapati, M. Gohain, B. J. Gogoi, Tetrahedron Lett. 2006, 47, 3535.
12. M. Rueping, B. J. Nachtsheim, W. Ieawsuwan, Adv. Synth. Catal. 2006, 348, 1033
13. P. Vicennati, P. G. Cozzi, Eur. J. Org. Chem. 2007, 2248
14. S. Shirakawa, S. Kobayashi, Org. Lett. 2007, 9, 311
15. J. Y. L. Chung, D. Mancheno, P. G. Dormer, N. Variankaval, R. G. Ball, N. N. Tsou, Org. Lett. 2008, 10, 3037.
16. J. S. Yadav, B. V. S. Reddy, K. V. R. Rao, G. G. K. S. Kumar, Tetrahedron Lett. 2007, 48, 5573
17. P. Srihari, D. C. Bhunia, P. Sreedhar, S. S. Mandal, J. S. S. R. Reddy, J. S. Yadav, Tetrahedron Lett. 2007, 48, 8120
18. R. Sanz, D. Miguel, J. M. Álvarez-Gutiérrez, F. Rodríguez, Synlett 2008, 975.
19. E. F. Pratt, L. W. Botimer, J. Am. Chem. Soc. 1957, 79, 5248
20. R. H. Cornforth, R. Robinson, J. Chem. Soc. 1942, 680.
21. Grigg and co-workers reported the use of iridium-catalyzed "hydrogen borrowing" to alkylate indole at C3 with primary benzylic and heterobenzylic alcohols. Two primary aliphatic alcohols were reported (three entries). In these instances, 0.2-2.0 equiv of KOH was required, the reaction time was 24-48 h at 110 °C, and yields were 35, 53, and 74 %. See:, S. Whitney, R. Grigg, A. Derrick, A. Keep, Org. Lett. 2007, 9, 3299.
22. E. F. Pratt, E. J. Frazza, J. Am. Chem. Soc. 1954, 76, 6174
23. K. L. Schoen, E. I. Becker, J. Am. Chem. Soc. 1955, 77, 6030
24. R. H. Cornforth, R. Robinson, J. Chem. Soc. 1942, 682.
25. C. F. de Graauw, J. A. Peters, H. van Bekkum, J. Huskens, Synthesis 1994, 1007
26. C. R. Graves, K. A. Scheidt, S. T. Nguyen, Org. Lett. 2006, 8, 1229.
27. J. R. Rizzo, C. A. Alt, T. Y. Zhang, Tetrahedron Lett. 2008, 49, 6749
28. L.-L. Cao, D.-S. Wang, G.-F. Jiang, Y.-G. Zhou, Tetrahedron Lett. 2011, 52, 2837.
29. F. A. Carey, R. J. Sundberg, Advanced Organic Chemistry Part A: Structure and Mechanisms, Springer Science+Business Media, New York, 2007, pp. 965-1071.
30. X. Han, H. Li, R. P. Hughes, J. Wu, Angew. Chem. 2012, 124, 10536
31. Angew. Chem. Int. Ed. 2012, 51, 10390.
32. K.-J. Haack, S. Hashiguchi, A. Fujii, T. Ikariya, R. Noyori, Angew. Chem. 1997, 109, 297
33. Angew. Chem. Int. Ed. Engl. 1997, 36, 285
34. E. J. Campbell, H. Zhou, S. T. Nguyen, Angew. Chem. 2002, 114, 1062
35. Angew. Chem. Int. Ed. 2002, 41, 1020
36. D. A. Evans, S. G. Nelson, M. R. Gagné, A. R. Muci, J. Am. Chem. Soc. 1993, 115, 9800.
37. L. Cronin, F. Manoni, C. J. O'Connor, S. J. Connon, Angew. Chem. 2010, 122, 3109
38. Angew. Chem. Int. Ed. 2010, 49, 3045
39. S. P. Curran, S. J. Connon, Angew. Chem. 2012, 124, 11024
40. Angew. Chem. Int. Ed. 2012, 51, 10866.
41. There is one example of an uncatalyzed MPVO reaction but requires 300 °C under supercritical conditions. See:, L. Sominsky, E. Rozental, H. Gottlieb, A. Gedanken, S. Hoz, J. Org. Chem. 2004, 69, 1492.
42. R. Kow, R. Nygren, M. W. Rathke, J. Org. Chem. 1977, 42, 826
43. K. G. Akamanchi, N. R. Varalakshmy, Tetrahedron Lett. 1995, 36, 3571
44. K. G. Akamanchi, N. R. Varalakshmy, B. A. Chaudhari, Synlett 1997, 371.
45. B. W. Gung, Tetrahedron 1996, 52, 5263
46. Y.-D. Wu, K. N. Houk, J. Am. Chem. Soc. 1987, 109, 906
47. Y.-D. Wu, K. N. Houk, J. Am. Chem. Soc. 1987, 109, 908.
48. CCDC 929479 (8 an) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.