Predictable and site-selective functionalization of poly(hetero)arene compounds by palladium catalysis

Journal of Organic Chemistry

Volumn 76, Issue 3, 2011, Pages 749-759

  Lapointe, David ^a   Markiewicz, Thomas ^a   Whipp, Christopher J ^a   Toderian, Amy ^a   Fagnou, Keith ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC SUBSTRATES; ARYLATIONS; BENZYLATION; C-H BOND; ELECTRON-RICH; FUNCTIONALIZATIONS; HETEROARENES; METALATIONS; MODEL SUBSTRATES; PALLADIUM CATALYSIS; PYRIDINE N-OXIDE; REACTION CONDITIONS; SITE SELECTIVE; SITE-SELECTIVITY;

AROMATIC COMPOUNDS; BENZENE; BENZENE REFINING;

CATALYSIS;

BENZENE DERIVATIVE; INDOLE DERIVATIVE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON; PYRIDINE 1 OXIDE;

ARTICLE; ARYLATION; BENZYLATION; CATALYSIS; CHEMICAL MODIFICATION; DENSITY FUNCTIONAL THEORY; DEPROTONATION; ELECTRON; HYDROGEN BOND; METALATION; PROTON TRANSPORT;

HETEROCYCLIC COMPOUNDS; HYDROCARBONS, FLUORINATED; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM; STEREOISOMERISM;

EID: 79851486610     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo102081a     Document Type: Article

References (55)

1. Daugulis, O.; Zaitsev, V. G.; Shabashov, D.; Pham, Q.-N.; Lazareva, A. Synlett 2006, 3382.
2. Campeau, L.-C.; Fagnou, K. Chem. Commun. 2006, 1253.
3. Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174.
4. Seregin, I. V.; Gevorgyan, V. Chem. Soc. Rev. 2007, 36, 1173.
5. Satoh, T.; Miura, M. Chem. Lett. 2007, 36, 200.
6. Campeau, L.-C.; Stuart, D. R.; Fagnou, K. Aldrichim. Acta 2007, 40, 35.
7. Li, B.-J.; Yang, S.-D.; Shi, Z.-J. Synlett 2008, 949.
8. Kakiuchi, F.; Kochi, T. Synthesis 2008, 3013.
9. McGlacken, G. P.; Bateman, L. M. Chem. Soc. Rev. 2009, 38, 2447.
10. Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094.
11. Kulkarni, A. A.; Daugulis, O. Synthesis 2009, 24, 4087.
12. Bellina, F.; Rossi, R. Tetrahedron 2009, 65, 10269.
13. Ackermann, L.; Vicente, R.; Kapdi, A. R. Angew. Chem., Int. Ed. 2009, 48, 9792.
14. Roger, J.; Gottumukkala, A. L.; Doucet, H. ChemCatChem 2010, 2, 20.
15. Thompson, M. J.; Borsenberger, V.; Louth, J. C.; Judd, K. E.; Chen, B. J. Med. Chem. 2009, 52, 7503.
16. Gavai, A. V.; Fink, B. E.; Fairfax, D. J.; Martin, G. S.; Rossiter, L. M.; Holst, C. L.; Kim, S.-H.; Leavitt, K. J.; Mastalerz, H.; Han, W.-C.; Norris, D.; Goyal, B.; Swaminathan, S.; Patel, B.; Mathur, A.; Vyas, D. M.; Tokarski, J. S.; Yu, C.; Oppenheimer, S.; Zhang, H.; Marathe, P.; Fargnoli, J.; Lee, F. Y.; Wong, T. W.; Vite, G. D. J. Med. Chem. 2009, 52, 6527.
17. Brak, K.; Kerr, I. D.; Barrett, K. T.; Fuchi, N.; Debnath, M.; Ang, K.; Engel, J. C.; McKerrow, J. H.; Doyle, P. S.; Brinen, L. S.; Ellman, J. A. J. Med. Chem. 2010, 53, 1763.
18. Lumeras, W.; Caturla, F.; Vidal, L.; Esteve, C.; Balagué, C.; Orellana, A.; Domínguez, M.; Roca, R.; Huerta, J. M.; Godessart, N.; Vidal, B. J. Med. Chem. 2009, 52, 5531.
19. Huestis, M. P.; Fagnou., K. Org. Lett. 2009, 11, 1357.
20. Campeau, L.-C.; Stuart, D. R.; Leclerc, J.-P.; Bertrand-Laperle, M.; Villemure, E.; Sun, H.-Y.; Laserre, S.; Guimond, N.; Lecavallier, M.; Fagnou,K. J. Am. Chem. Soc. 2009, 131, 3291.
21. Schipper, D. J.; El-Salfiti, M.; Whipp, C. J.; Fagnou, K. Tetrahedron 2009, 65, 4977.
22. Schipper, D. J.; Campeau, L.-C.; Fagnou, K. Tetrahedron 2009, 65, 3155.
23. Campeau L.-C.; Schipper, D. J.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 3266.
24. Campeau, L.-C.; Bertrand-Laperle, M.; Leclerc, J.-P.; Villemure, E.; Gorelsky, S. I.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 3276.
25. Leclerc J.-P.; Fagnou, K. Angew. Chem., Int. Ed. 2006, 45, 7781.
26. Campeau, L.-C.; Rousseaux, S.; Fagnou, K. J. Am. Chem. Soc. 2005, 127, 18020.
27. Lebrasseur, N.; Larrosa, I. J. Am. Chem. Soc. 2008, 130, 2926.
28. René, O.; Fagnou, K. Org. Lett. 2010, 12, 2116.
29. Lafrance, M.; Shore, D.; Fagnou, K. Org. Lett. 2006, 8, 5097.
30. Lafrance, M.; Rowley, C. N.; Woo, T. K.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 8754.
31. Phipps, R. J.; Grimster, N. P.; Gaunt, M. J. J. Am. Chem. Soc. 2008, 130, 8172.
32. See the Supporting Information for details.
33. Contrary to the report on azaindoles (see ref 6), in which the functionalization of the azole ring gave better yields when the unactivated azine ring was used compared to the yields obtained when the azine ring was activated as the N-oxide.
34. For a review on the mechanistic work done on theCMDmechanism, see:
35. Lapointe, D.; Fagnou, K. Chem. Lett. 2010, 39, 1118.
36. For the seminal mechanistic studies in catalytic settings, see:
37. González, J. J.; García, N.;Gómez-Lor, B.; Echavarren, A. M. J. Org. Chem. 1997, 62, 1286.
38. Campeau, L.-C.; Parisien, M.; Leblanc, M.; Fagnou, K. J. Am. Chem. Soc. 2004, 126, 9186.
39. Campeau, L.-C.; Parisien, M.; Jean, A.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 581.
40. García-Cuadrado, D.; Braga, A. A. C.; Maseras, F.; Echavarren, A. M. J. Am. Chem. Soc. 2006, 128, 1066.
41. For examples of studies utilizing p-trifluromethylphenyl groups and 19F NMR spectroscopy, see:
42. Geyer, A. M.; Wiedner, E. S.; Gary, J. B.; Gdula, R. L.; Kuhlmann, N. C.; Johnson, M. J. A.; Dunietz, B. D.; Kampf, J. W. J. Am. Chem. Soc. 2008, 130, 8984. For other recent examples of mechanistic studies utilizing 19F NMR spectroscopy, see:
43. Viciu, M. S.; Gupta, L.; Collum, D. B. J. Am. Chem. Soc. 2010, 132, 6361.
44. De Vries, T. S.; Goswami, A.; Liou, L. R.; Gruver, J. M.; Jayne, E.; Collum, D. B. J. Am. Chem. Soc. 2009, 131, 13142.
45. Gupta, L.; Hoepker, A. C.; Singh, K. J.; Collum, D. B. J. Org. Chem. 2009, 74, 2231.
46. Park, C.-H.; Ryabova, V.; Seregin, I. V.; Sromek, A. W.; Gevorgyan, V. Org. Lett. 2004, 6, 1159.
47. As one of our reviewers pointed out, a close examination of the various product ratios reveals that the ratios are not always cumulative when the reactivity of the heteroarenes are compared. Certainly, it is a very interesting observation, and it would be worth examining in detail; however, at the moment we cannot propose an explanation
48. Lapointe, D.; Fagnou, K. Org. Lett. 2009, 11, 4160.
49. Soll, R. M.; Parks, J. A.; Rimele, T. J.; Heaslip, R. J.; Wojdan, A.; Oshiro, G.; Grimes, D.; Asselin, A. Eur. J. Org. Chem. 1990, 25, 191.
50. Taikyun, R.; Lankin, M. E.; Shih, D. H.; Lankin, C. M. Synthesis of 2-(2-furoyl)-4(5)-(2-furanyl)-1H-imidazole and analogs thereof. U.S. Patent 4665192, May 1987.
51. Turner, G. L.; Morris, J. A.; Greaney, M. F. Angew. Chem., Int. Ed. 2007, 46, 7996.
52. Rivall, Y.; Grassy, G.; Taudou, A.; Ecalle, R. J. Med. Chem. 1991, 26, 13.
53. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596.
54. Bonini,C.;Chiummiento,L.;DeBonis,M.;Funicello,M.;Lupattelli, P.; Pandolfo, R. Tetrahedron: Asymmetry 2006, 17, 2919.
55. Zhang, L.; Liang, F.; Sun, L.; Hu, Y.; Hu,HSynthesis 2000, 12, 1733.