Palladium-catalyzed direct C-H arylation of N-iminopyridinium ylides: Application to the synthesis of (±)-anabasine

Journal of the American Chemical Society

Volumn 130, Issue 1, 2008, Pages 52-54

  Larivée, Alexandre ^a   Mousseau, James J ^a   Charette, André B ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANABASINE; PYRIDINIUM DERIVATIVE;

ARTICLE; ARYLATION; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; SYNTHESIS;

ANABASINE; CATALYSIS; HYDROCARBONS, AROMATIC; INSECTICIDES; PALLADIUM; PIPERIDINES; PYRIDINES;

EID: 38348998675     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja710073n     Document Type: Article

References (42)

1. For recent reviews on the stereoselective synthesis of piperidines see: (a) Buffat, M. G. P. Tetrahedron 2004, 60, 1701.
2. (b) Felpin, F.-X.; Lebreton, J. M. Eur. J. Org. Chem. 2003, 3693.
3. (c) Weintraub, P. M.; Sabol, J. S.; Kane, J. M.; Borcherding, D. R. Tetrahedron 2003, 59, 2953.
4. (a) Larivée, A.; Charette, A. B. Org. Lett. 2006, 8, 3955.
5. (b) Sales, M.; Charette, A. B. Org. Lett. 2005, 7, 5773.
6. (c) Charette, A. B.; Mathieu S.; Martel, J. Org. Lett. 2005, 7, 5401.
7. (d) Lemire, A.; Charette, A. B. Org. Lett. 2005, 7, 2747.
8. (e) Lemire, A.; Beaudoin, D.; Grenon, M.; Charette, A. B. J. Org. Chem. 2005, 70, 2368.
9. (f) Lemire, A.; Grenon M.; Pourashraf, M.; Charette, A. B. Org. Lett. 2004, 6, 3517.
10. (a) Legault, C. Y.; Charette, A. B. J. Am. Chem. Soc. 2003, 125, 6360.
11. (b) Charette, A. B.; Grenon, M.; Lemire, A.; Pourashraf, M.; Martel, J. J. Am. Chem. Soc. 2001, 123, 11829.
12. Legault. C. Y.; Charette, A. B. J. Am. Chem. Soc. 2005, 127, 8966.
13. (a) Molander, G. A.; Biolatto, B. J. Org. Chem. 2003, 68, 4302.
14. (b) Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020.
15. Andersson, H.; Almqvist, F.; Olsson, R. Org. Lett. 2007, 9, 1335.
16. (a) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174.
17. (b) LeClerc, J.-P.; Fagnou, K. Angew. Chem., Int. Ed. 2006, 45, 7781.
18. (c) Garcia-Cuadrado, D.; Braga, A. A. C.; Maseras, F.; Echavarren, A. M. J. Am. Chem. Soc. 2006, 128, 1066.
19. (d) Miura, M.; Satoh, T. Top. Organomet. Chem. 2005, 14, 55.
20. (e) Wolfe, J. P.; Thomas, J. S. Curr. Org. Chem. 2005, 9, 625.
21. (f) Kakiuchi, F.; Chatani, N. Adv. Synth. Catal. 2003, 345, 1077.
22. (g) Miura, M.; Nomura, M. Top. Curr. Chem. 2002, 219, 211.
23. (h) Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1698.
24. (a) Ackermann, L.; Althammer, A.; Born, R.; Angew. Chem. Int. Ed. 2006, 45, 2619.
25. (b) Campeau, L.-C.; Rousseaux, S.; Fagnou, K. J. Am. Chem. Soc. 2005, 127, 18020.
26. (c) Jonkers, T. H. M.; Maes, B. U. W.; Lemrère, G. L. F.; Rombouts, G.; Pieters, L.; Haemers, A.; Dommisse, R. A. Synlett 2003, 5, 615.
27. (d) Or, S.; Fukita, S.; Hirata, N.; Watanuki, N.; Mryano, S.; Inoue, Y. Org. Lett. 2001, 3, 2579.
28. (e) Mukhopadhyay S.; Rothenberg, G.; Gitis, D.; Baidossi, M.; Ponde, D. E.; Sasson, Y. Perkin Trans. 2 2000, 1809.
29. (f) Oi, S.; Fukita, S.; Inoue, Y. Chem. Commun. 1998, 2439.
30. (g) Albrecht, K.; Reiser, O.; Weber, M.; Knieriem, B.; De Merjere, A. Tetrahedron 1994, 50, 383.
31. (h) Ames, D. E.; Opalko, A. Tetrahedron 1984, 40, 1919.
32. For the direct alkylation of pyridines see: (i) Lewis J. C.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2007, 129, 5332.
33. For examples of catalytic ortho-arylation of arylamides and anilides see: (a) Okazawa, T.; Satoh, T.; Miura, M.; Nomura, M. J. Am. Chem. Soc. 2002, 124, 5286.
34. (b) Daugulis, O.; Zaitsev, V. G. Angew. Chem., Int. Ed. 2005, 44, 4046.
35. (c) Yang, S.; Li, B.; Wan, X.; Shi, Z. J. Am. Chem. Soc. 2007, 129, 6066.
36. Legault, C.; Charette, A. B. J. Org. Chem. 2003, 68, 7119.
37. For recent syntheses of anabasine, see: (a) Amat, M.; Cantó, M.; Llor, N.; Bosch, J. Chem. Commun. 2002, 526.
38. (b) Barco, A.; Benetti, S.; De Risi, C.; Marchetti, P.; Pollini, G. P.; Zanirato, V. Eur. J. Org. Chem. 2001, 975.
39. (c) Felpin, F.-X.; Girard, S.; Vo-Thanh, G.; Robinis, R. J.; Villiéras, J.; Lebreton, J. J. Org. Chem. 2001, 66, 6305.
40. (d) Andrés, J. M.; Herráiz-Sierra, I.; Pedrosa, R.; Pérez-Encabo, A. Eur. J. Org. Chem. 2000, 1719.
41. Martínez-Barrasa, V.; Delgado, F.; Burgos, C.; García-Navío, J. L.; Izquierdo, M. L.; Alvarez-Builla, J. Tetrahedron 2000, 56, 2481.
42. García de Viedma, A.; Martínez-Barrasa, V.; Burgos, C.; Izquierdo, M. L.; Alvarez-Builla, J. J. Org. Chem. 1999, 64, 1007.