Oxidative palladium catalysis in SNAr reactions leading to heteroaryl ethers from pyridotriazol-1-yloxy heterocycles with aryl boronic acids

Journal of the American Chemical Society

Volumn 131, Issue 12, 2009, Pages 4174-4175

  Wacharasindhu, Sumrit ^a,b   Bardhan, Sujata ^a,b   Wan, Zhao Kui ^a,b   Tabei, Keiko ^a,b   Mansour, Tarek S ^a,b  

^a WYETH RESEARCH   (United States)

^b NONE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CESIUM COMPOUNDS; ETHERS; PALLADIUM; PALLADIUM COMPOUNDS; REACTION INTERMEDIATES; SULFUR COMPOUNDS;

ARYL BORONIC ACIDS; BENZOTRIAZOLES; MECHANISTIC STUDIES; NONOXIDATIVE PATHWAY; OXIDATIVE COUPLINGS; PALLADIUM CATALYSIS; PALLADIUM-CATALYZED; THIENOPYRIMIDINES;

NITROGEN COMPOUNDS;

BORONIC ACID DERIVATIVE; ETHER DERIVATIVE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRIMIDINE DERIVATIVE; QUINAZOLINE DERIVATIVE; NITROGEN; OXYGEN; PHENOL; SULFUR;

ARTICLE; ARYLATION; CATALYSIS; CROSS COUPLING REACTION; OXIDATION; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; ORGANIC CHEMISTRY; PROCEDURES; TIME;

BORONIC ACIDS; CATALYSIS; CHEMISTRY, ORGANIC; ETHERS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; NITROGEN; OXYGEN; PALLADIUM; PHENOL; PYRIMIDINES; QUINAZOLINES; SULFUR; TIME FACTORS;

EID: 67749139798     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja808622z     Document Type: Article

References (22)

1. (a) Schlummer, B.; Scholz, U. U. Adv. Synth. Catal. 2004, 346, 1599.
2. (b) Hartwig, J. F. Synlett 2006, 9, 1283.
3. Stahl, S. S. Angew. Chem., Int. Ed. 2004, 43, 3400.
4. Liebeskind, L. S.; Srogl, J. Org. Lett. 2002, 4, 979.
5. Leclerc, J.-P.; Fagnou, K. Angew. Chem., Int. Ed. 2006, 45, 7781.
6. (a) Wan, Z.-K.; Binnum, E.; Wilson, D. P.; Lee, J. Org. Lett. 2005, 7, 5877.
7. (b) Wan, Z.-K.; Wacharasindhu, S.; Binnum, E.; Mansour, T. Org. Lett. 2006, 8, 2425.
8. (c) Levins, C. G.; Wan, Z.-K. Org. Lett. 2008, 10, 1755.
9. Wan, Z.-K.; Wacharasindhu, S.; Levins, C.; Lin, M.; Tabei, K.; Mansour, T. S. J. Org. Chem. 2007, 72, 10194.
10. Kang, F.-A.; Sui, Z.; Murray, W. V. J. Am. Chem. Soc. 2008, 130, 11300.
11. 6-(benzotriazol-1-yl)inosine derivatives, see: Bae, S.; Lakshman, M. K. J. Org. Chem. 2008, 73, 1311.
12. Alsina, J.; Giralt, E.; Albericio, F. Tetrahedron Lett. 1995, 36, 4195.
13. (a) Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400.
14. (b) Chan, D. M. T.; Lam, P. Y. S. Boronic Acids; Hall, D. G., Ed.; Wiley-VCH: Weinheim, Germany, 2005; p 205.
15. 2 does not undergo reductive elimination to phenols.
16. 2Ar is possible; see: (a) Keith, J. M.; Nielsen, R. J.; Oxgaard, J.; Goddard, W. A., III. J. Am. Chem. Soc. 2005, 127, 13172.
17. (b) Denney, M. C.; Smythe, N. A.; Cetto, K. L.; Kemp, R. A.; Goldberg, K. I. J. Am. Chem. Soc. 2006, 128, 2508.
18. Popp, B. V.; Stahl, S. S. J. Am. Chem. Soc. 2006, 128, 2804.
19. Yoo, K. S.; Yoon, C. H.; Jung, K. W. J. Am. Chem. Soc. 2006, 128, 16384.
20. 2. See: (a) Hatamoto, Y.; Sakaguchi, S.; Ishii, Y. Org. Lett. 2004, 6, 4623.
21. (b) Yamamoto, Y.; Suzuki, R.; Hattori, K.; Nishiyama, H. Synlett 2006, 1027. Also see refs 7, 11, and 13.
22. Pd-catalyzed arylation of 2-pyridone with aryl halides gives N- and O-arylated products. See: Altman, R. A.; Buchwald, S. L. Org. Lett. 2007, 9, 643.