4,4′,4′-trimethyl-2,2′:6′,2′-terpyridine by oxidative coupling of 4-picoline

Journal of Organic Chemistry

Volumn 79, Issue 21, 2014, Pages 10624-10628

  Robo, Michael T ^a   Prinsell, Michael R ^a   Weix, Daniel J ^a  

^a UNIVERSITY OF ROCHESTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHELATION; MANGANESE OXIDE;

4-PICOLINE; BIPYRIDINES; DEHYDROGENATIVE COUPLING; OXIDATIVE COUPLINGS; SELECTIVE FORMATION; TERPYRIDINES; TRIMETHYL;

SYNTHESIS (CHEMICAL);

4 PICOLINE; 4,4',4'' TRIMETHYL 2,2':6',2'' TERPYRIDINE; CARBON; ELECTROPHILE; MANGANESE DIOXIDE; PALLADIUM; PICOLINE DERIVATIVE; PIVALIC ACID; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG; 4,4',4''-TRI-TERT-BUTYL-2,2'-6',2''-TERPYRIDINE; MANGANESE DERIVATIVE; MANGANESE OXIDE; OXIDE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; COVALENT BOND; OXIDATIVE COUPLING; OXIDATIVE DEHYDROGENATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION TIME; SYNTHESIS; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY;

CATALYSIS; MANGANESE COMPOUNDS; MOLECULAR STRUCTURE; OXIDATIVE COUPLING; OXIDES; PALLADIUM; PICOLINES; PYRIDINES;

EID: 84910010890     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo501925s     Document Type: Article

References (43)

1. Kröhnke, F. Synthesis 1976, 1976, 1-24
2. Cargill Thompson, A. M. W. Coord. Chem. Rev. 1997, 160, 1-52
3. Chelucci, G.; Thummel, R. P. Chem. Rev. 2002, 102, 3129-3170
4. Thummel, R. P., Terpyridine, Oligopyridine, and Polypyridine Ligands. In Comprehensive Coordination Chemistry II; McCleverty, J. A.; Meyer, T. J., Eds.; Pergamon: Oxford, 2003; pp 41-53.
5. Bonhôte, P.; Moser, J.-E.; Humphry-Baker, R.; Vlachopoulos, N.; Zakeeruddin, S. M.; Walder, L.; Grätzel, M. J. Am. Chem. Soc. 1999, 121, 1324-1336
6. Feldhiem, D. L.; Baldy, C. J.; Sebring, P.; Hendrickson, S. M.; Elliot, C. M. J. Electrochem. Soc. 1995, 142, 3366-3372
7. Nazeeruddin, K. M.; Pechy, P.; Grätzel, M. Chem. Commun. 1997, 34, 1705-1706
8. For a nice direct synthesis of 1b, see: Dehaudt, J.; Husson, J.; Guyard, L. Green Chem. 2011, 13, 3337-3340
9. Anderson, T. J.; Jones, G. D.; Vicic, D. A. J. Am. Chem. Soc. 2004, 126, 8100-8101
10. Jones, G. D.; McFarland, C.; Anderson, T. J.; Vicic, D. A. Chem. Commun. 2005, 4211-4213
11. Jones, G. D.; Martin, J.; McFarland, C.; Allen, O.; Hall, R.; Haley, A.; Brandon, R.; Konovalova, T.; Desrochers, P.; Pulay, P.; Vicic, D. J. Am. Chem. Soc. 2006, 128, 13175-13183
12. Gong, H.; Gagné, M. J. Am. Chem. Soc. 2008, 130, 12177-12183
13. Zhang, C.-P.; Wang, H.; Klein, A.; Biewer, C.; Stirnat, K.; Yamaguchi, Y.; Xu, L.; Gomez-Benitez, V.; Vicic, D. A. J. Am. Chem. Soc. 2013, 135, 8141-8144
14. Prinsell, M. R.; Everson, D. A.; Weix, D. J. Chem. Commun. 2010, 46, 5743-5745
15. Shrestha, R.; Weix, D. J. Org. Lett. 2011, 13, 2766-2769
16. Anka-Lufford, L. L.; Prinsell, M. R.; Weix, D. J. J. Org. Chem. 2012, 77, 9989-10000
17. Ben Hadda, T.; Le Bozec, H. Polyhedron 1988, 7, 575-577
18. Potts, K. T. Bull. Soc. Chim. Belg. 1990, 99, 741
19. Fallahpour, R.-A. Synthesis 2000, 1665-1667
20. Heller, M.; Schubert, U. S. Eur. J. Org. Chem. 2003, 947-961
21. Duric, S.; Sypaseuth, F. D.; Hoof, S.; Svensson, E.; Tzschucke, C. C. Chem. - Eur. J. 2013, 19, 17456-17463
22. Rosevear, P. E.; Sasse, W. H. F. J. Heterocycl. Chem. 1971, 8, 483-485
23. Munavalli, S.; Grätzel, M. Chem. Ind. (London) 1987, 51, 722-724
24. Hagelin, H.; Hedman, B.; Orabona, I.; Åkermark, T.; Åkermark, B.; Klug, C. A. J. Mol. Catal. A: Chem. 2000, 164, 137-146
25. Neal, L. M.; Everett, M. L.; Hoflund, G. B.; Hagelin-Weaver, H. E. J. Mol. Catal. A: Chem. 2011, 335, 210-221
26. Badger, G. M.; Sasse, W. H. F. J. Chem. Soc. 1956, 616-620
27. Sasse, W. H. F.; Snieckus, V. A.; Boekelheide, V. Org. Synth. 1966, 46, 5
28. Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879-2932
29. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147-1169
30. Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215-1292
31. Takacs, J.; Jiang, X. Curr. Org. Chem. 2003, 7, 369-396
32. Popp, B. V.; Stahl, S. S. Palladium-Catalyzed Oxidation Reactions: Comparison of Benzoquinone and Molecular Oxygen as Stoichiometric Oxidants. In Organometallic Oxidation Catalysis, Meyer, F.; Limberg, C., Eds. Springer: Berlin, 2007; Vol. 22, pp 149-189.
33. Desai, L. V.; Malik, H. A.; Sanford, M. S. Org. Lett. 2006, 8, 1141-1144
34. Zhao, J.; Asao, N.; Yamamoto, Y.; Jin, T. J. Am. Chem. Soc. 2014, 136, 9540-9543
35. Cahiez, G.; Alami, M.; Taylor, R. J. K.; Reid, M.; Foot, J. S.; Fader, L., Manganese Dioxide. In Encyclopedia of Reagents for Organic Synthesis; John Wiley & Sons, Ltd.: New York, 2001.
36. Sasse, W. H. F.; Whittle, C. P. J. Chem. Soc. 1961, 1347-1350
37. Polin, J.; Schmohel, E.; Balzani, V. Synthesis 1998, 1998, 321-324
38. Kawashima, T.; Takao, T.; Suzuki, H. J. Am. Chem. Soc. 2007, 129, 11006-11007
39. Takao, T.; Kawashima, T.; Kanda, H.; Okamura, R.; Suzuki, H. Organometallics 2012, 31, 4817-4831
40. Beley, M.; Collin, J.-P.; Sauvage, J.-P.; Sugihara, H.; Heisel, F.; Miehe, A. J. Chem. Soc., Dalton Trans. 1991, 3157-3159
41. Szpakolski, K.; Latham, K.; Rix, C.; Rani, R. A.; Kalantar-zadeh, K. Polyhedron 2013, 52, 719-732
42. Rossi, R. A.; Postigo, A. Org. Lett. 2001, 3, 1197-1200
43. Hua, S.-K.; Hu, Q.-P.; Ren, J.; Zeng, B.-B. Synthesis 2013, 45, 518-526