Indole synthesis: palladium-catalyzed C-H bond amination via reduction of nitroalkenes with carbon monoxide

Tetrahedron

Volumn 65, Issue 16, 2009, Pages 3062-3068

  Hsieh, Tom H H ^a   Dong, Vy M ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

Carbon monoxide; Indole; Nitroalkene; Palladium catalysis

Indexed keywords

ALKENE; CARBON DIOXIDE; CARBON MONOXIDE; INDOLE; NITROALKENE; NITROSO DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL BOND; CYCLIZATION; PRIORITY JOURNAL; REDUCTION; STOICHIOMETRY; SYNTHESIS;

CHAMAELEONIDAE;

EID: 62049084389     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.11.034     Document Type: Article

References (69)

1. Nicolaou K.C., and Sorensen E.J. Classics in Total Synthesis (1996), Wiley-VCH, Weinheim
2. Hartwig J.F. In: Negishi E. (Ed). Handbook of Organopalladium Chemistry for Organic Synthesis (2002), Wiley-Interscience, New York, NY 1051
3. Jiang L., and Buchwald S.L. In: de Meijere A., and Diederich F. (Eds). Metal-Catalyzed Cross-Coupling Reactions. 2nd Ed. (2004), Wiley-VCH, Weinheim 699
4. Espino C.G., and DuBois J. In: Evans P.A. (Ed). Modern Rhodium-Catalyzed Organic Reactions (2005), Wiley-VCH, Weinheim 379
5. Fiori K.W., and Du Bois J. J. Am. Chem. Soc. 129 (2007) 562
6. Fiori K.W., Fleming J.J., and Du Bois J. Angew. Chem., Int. Ed. 43 (2004) 4349
7. Espino C.G., When P.M., Chow J., and Du Bois J. J. Am. Chem. Soc. 123 (2001) 6935
8. For applications in synthesis, see:
9. Conrad R.M., and Du Bois J. Org. Lett. 9 (2007) 5465
10. Fleming J.J., McReynolds M.D., and Du Bois J. J. Am. Chem. Soc. 129 (2007) 9964
11. Hinman A., and Du Bois J. J. Am. Chem. Soc. 125 (2003) 11510
12. Gowenlock B.G., and Richter-Addo G.B. Chem. Rev. 104 (2004) 3315
13. Gilchrist T.L. Chem. Soc. Rev. 1 (1983) 53
14. Francote E., Merényi R., Vandenbulcke-Coyette B., and Viehe H.G. Helv. Chim. Acta 64 (1981) 1208
15. Söderberg B.C.G. Curr. Org. Chem. 4 (2000) 727
16. L'abbé G. Angew. Chem., Int. Ed. Engl. 14 (1975) 775
17. For reviews on metal-imidos (nitrenoids), see:
18. Davies H.M.L., and Manning J.R. Nature 451 (2008) 417
19. Ref. 2.
20. For a review on conjugated nitroalkenes as synthetic intermediates, see:. Barrett A.G.M., and Graboski G.G. Chem. Rev. 86 (1986) 751
21. For applications of CO, see:
22. Alper H., and Grushin V. J. Am. Chem. Soc. 117 (1995) 4305
23. Colquhoun H.M., Thompson D.J., and Twigg M.V. Carbonylation: Direct Synthesis of Carbonyl Compounds (1991), Plenum, New York, NY
24. Tafesh A.M., and Weiguny J. Chem. Rev. 96 (1996) 2035
25. Ragaini F., Cenini S., Gallo E., Caselli A., and Fantauzzi S. Curr. Org. Chem. 10 (2006) 1479
26. Paul F., Fischer J., Ochsenbein P., and Osborn J.A. Compt. Rendus Chem. 5 (2002) 267
27. Ragaini F., Sportiello P., and Cenini S. J. Organomet. Chem. 577 (1999) 283
28. Ragaini F., and Cenini S. J. Mol. Catal. A: Chem. 109 (1996) 1
29. Wehman P., Kaasjager V.E., de Lange W.G.J., Hartl F., Kamer P.C.J., and van Leeuwen P.W.N.M. Organometallics 14 (1995) 3751
30. Wehman P., Dol G.C., Moorman E.R., Kamer P.C.J., and van Leeuwen P.W.N.M. Organometallics 13 (1994) 4856
31. For examples of metal-mediated carbazole formation from corresponding ortho-nitrobiaryls, see:
32. Smitrovich J.H., and Davies I.W. Org. Lett. 6 (2004) 533
33. Pizzotti M., Cenini S., Quici S., and Tollari S. J. Chem. Soc., Perkin Trans. 2 (1994) 913
34. Crotti C., Cenini S., Bassoli A., Rindone B., and Demartin F. J. Mol. Catal. 70 (1991) 175
35. For examples of metal-free phosphite and phosphine reduction of ortho-nitrobiaryls and ortho-nitrostyrenes to carbazoles and indoles, respectively, see:
36. Cadogan J.I.G., Cameron-Wood M., Mackie R.K., and Searle R.J.G. J. Chem. Soc. (1965) 4831
37. Sundberg R.J. J. Org. Chem. 30 (1965) 3604
38. Freeman A.W., Urvoy M., and Criswell M.E. J. Org. Chem. 70 (2005) 5014
39. For examples of metal-free phosphite reduction of nitroalkenes to indoles, see:
40. Russell G.A., Yao C.F., Tashtoush H.I., Russell J.E., and Dedolph D.F. J. Org. Chem. 56 (1991) 663
41. Russell G.A., and Yao C.F. J. Org. Chem. 57 (1992) 6508
42. Russell G.A., and Yao C.F. Heteroat. Chem. 3 (1992) 209
43. For extensive reviews of indole syntheses, see:
44. Shivaputra P., and Buolamwini J.K. Curr. Org. Chem. 3 (2006) 477
45. Humphrey G.R., and Kuethe J.T. Chem. Rev. 106 (2006) 2875
46. For specific examples of indole syntheses involving carbon-substituted benzenes, see:
47. Chiba S., Hattori G., and Narasaka K. Chem. Lett. 36 (2007) 52
48. Taber D.F., and Tian W. J. Am. Chem. Soc. 128 (2006) 1058
49. Du Y., Liu R., Linn G., and Zhao K. Org. Lett. 8 (2006) 5919
50. Carpenter J.F. J. Org. Chem. 58 (1993) 1607
51. Lim M.I., and Patil D.G. Tetrahedron Lett. 28 (1987) 3775
52. 2-bound to a Pt center (intermediate 5), see:. Pizzotti M., Porta F., Cenini S., Demartin F., and Masciocchi N. J. Organomet. Chem. 330 (1987) 265
53. For experimental and theoretical mechanistic studies involving nitroarenes systems, see:
54. Leach A.G., Houk K.N., and Davies I.W. Synthesis (2005) 3463
55. Davies I.W., Smitrovich J.H., Sidler R., Qu C., Gresham V., and Bazaral C. Tetrahedron 61 (2005) 6425
56. Davies I.W., Guner V.A., and Houk K.N. Org. Lett. 6 (2004) 743
57. N-Hydroxyindole derivatives afford the reduced 1H-indole product under reductive carbonylation conditions: See Ref. 17b.
58. We favor the nitrosoalkene mechanism on the basis of mechanistic studies involving nitroarenes. See Ref. 17 for details.
59. Stokes B.J., Dong H., Brooke B.E., Pumphrey A.L., and Driver T.G. J. Am. Chem. Soc. 129 (2007) 7500
60. Dong H., Shen M., Redford J.E., Stokes B.J., Pumphrey A.L., and Driver T.G. Org. Lett. 9 (2007) 5191
61. Shen M., Leslie B.E., and Driver T.G. Angew. Chem., Int. Ed. 47 (2008) 5056
62. See Supplementary data for other metals and conditions tested.
63. DMF resulted in the best GC conversions among the following solvents: NMP, DMSO, toluene, benzene, 1,4-dioxane, and MeCN.
64. See Section 4 and Supplementary data for details regarding the preparation of the nitroalkene substrates.
65. See Supplementary data for the molecular structure of 8m and its X-ray crystallographic data. Structure was rendered using Persistence of Vision Raytracer (Version 3.6) retrieved from http://www.povray.org/download/.
66. Perrin D.D., and Armarego W.L.F. Purification of Laboratory Chemicals. 5th ed. (1988), Pregamon, Oxford
67. Gosselin F., O'Shea P.D., Roy S., Reamer R.A., Chen C., and Volante R.P. Org. Lett. 7 (2005) 355
68. Charles G. Bull. Soc. Chim. Fr. (1963) 1573
69. Jia Y., and Zhu J. J. Org. Chem. 71 (2006) 7826