Ruthenium catalyzed decarbonylative arylation at sp3 carbon centers in pyrrolidine and piperidine heterocycles

Journal of the American Chemical Society

Volumn 129, Issue 38, 2007, Pages 11750-11755

  Gribkov, Denis V ^a   Pastine, Stefan J ^a   Schnürch, Michael ^a   Sames, Dalibor ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CATALYSIS; ESTERS; MIXTURES; RUTHENIUM;

ARYLBORONIC ACIDS; DECARBONYLATIVE ARYLATION; PIPERIDINE HETEROCYCLES; PYRROLIDINE;

AROMATIC COMPOUNDS;

AMIDINE; BORONIC ACID DERIVATIVE; HETEROCYCLIC COMPOUND; HYDROXYPROLINE; PIPERIDINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PROLINE DERIVATIVE; PYRROLIDINE DERIVATIVE; RUTHENIUM;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE;

BORONIC ACIDS; CARBON; CATALYSIS; ESTERS; HYDROCARBONS, AROMATIC; HYDROXYPROLINE; KETONES; MODELS, CHEMICAL; PIPERIDINES; PROLINE; PYRROLIDINES; RUTHENIUM; STEREOISOMERISM;

EID: 34748916010     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja072577n     Document Type: Article

References (23)

1. 2-Arylpyrrolidines and piperidines exhibit potent biological activity, particularly in the CNS. For examples, see: Elliot, R. L.; Kopeka, H.; Lin, N.-H.; He, Y.; Garvey, D. S. Synthesis 1995, 772-774.
2. For an excellent recent review, see: Campos, K. R. Chem. Soc. Rev. 2007, 36, 1069-1084.
3. Davies, H. M. L.; Venkataramani, C.; Hansen, T.; Hopper, D. W. J. Am. Chem. Soc. 2003, 125, 6462-6468.
4. Pastine, S. J.; Gribkov, D. V.; Sames, D. J. Am. Chem. Soc. 2006, 128, 14220-14221.
5. Lin, Y.-S.; Yamamoto, A. In Activation of Unreactive Bonds and Organic Synthesis; Murai, S., Ed.; Springer: Berlin, Germany 1999; pp 161-192.
6. (a) Chatani, N.; Tatamidani, H.; Ie, Y.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 2001, 123, 4849-4850.
7. (b) Tatamidani, H.; Yokota, K.; Kakiuchi, F.; Chatani, N. J. Org. Chem. 2004, 69, 5615-5621.
8. (c) Ruthenium-mediated decarbonylation of methyl benzoate (unactivated ester) has been reported: Hiraki, K.; Kira, S.; Kawano, H. Bull. Chem. Soc. Jpn. 1997, 70, 1583-1592.
9. (a) Kakino, R.; Shimizu, I.; Yamamoto, A. Bull. Chem. Soc. Jpn. 2001, 74, 371-376.
10. (b) Tatamidani, H.; Kakiuchi, F.; Chatani, N. Org. Lett. 2004, 6, 3597-3599.
11. For synthesis of ketones via palladium-catalyzed coupling of thioesters and boronic acids, see: Liebeskind, L. S.; Srogl, J. J. Am. Chem. Soc. 2000, 122, 11260-11261.
12. Gooßen, L. J.; Paetzold, J. Angew. Chem., Int. Ed. 2002, 41, 1237-1241.
13. (a) Gooßen, L. J.; Paetzold, J. Adv. Synth. Catal. 2004, 346, 1665-1668.
14. (b) O'Brien, E. M.; Bercot, E. A.; Rovis, T. J. Am. Chem. Soc. 2003, 125, 10498-10499.
15. (a) Burger, E. C.; Tunge, J. A. J. Am. Chem. Soc. 2006, 128, 10002-10003.
16. (b) Rayabarapu, D. K.; Tunge, J. A. J. Am. Chem. Soc. 2005, 127, 13510-13511 and references therein.
17. (c) Mohr, J. T.; Nishimata, T.; Behenna, D. C.; Stoltz, B. M. J. Am. Chem. Soc. 2006, 128, 11348-11349.
18. (d) Kuwano, R.; Yokogi, M. Chem. Commun. 2005, 5899-5901.
19. (a) Catalytic decarboxylative arylation of free carboxylic acids with haloarenes has recently been reported: Forgione, P.; Brochu, M.-C.; St-Onge, M.; Thesen, K. H.; Bailey, M. D.; Bilodeau, F. J. Am. Chem. Soc. 2006, 128, 11350-11351.
20. (b) Gooßen, L. J.; Deng, G.; Levy, L. M. Science 2006, 133, 662-664.
21. Catalytic cross-coupling of free arene carboxylic acids with alkenes (decarboxylative olefination): (c) Myers, A. G.; Tanaka, D.; Mannion, M. R. J. Am. Chem. Soc. 2002, 124, 11250-11251.
22. (d) Tanaka, D.; Romeril, S. P.; Myers, A. G. J. Am. Chem. Soc. 2005, 127, 10323-10333.
23. Kakiuchi, F.; Chatani, N. Adv. Synth. Catal. 2003, 345, 1077-1101.