Synthesis of dihydrobenzofurans via palladium-catalyzed annulation of 1,3-dienes by o -iodoaryl acetates

Journal of Organic Chemistry

Volumn 75, Issue 12, 2010, Pages 4131-4134

  Rozhkov, Roman V ^a   Larock, Richard C ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYL GROUPS; ARYL IODIDES; ARYLPALLADIUM COMPLEXES; DIHYDROBENZOFURANS; ELECTRON-DEFICIENT; ELECTRON-RICH; INTRAMOLECULAR COORDINATION; OXIDATIVE ADDITIONS; PHENOLIC OXYGEN; REDUCTIVE ELIMINATION; REGIO-SELECTIVE; STEREO-SELECTIVE; SYN-ADDITION;

COORDINATION REACTIONS; OLEFINS; ORGANOMETALLICS; OXYGEN; PALLADIUM; PHENOLS; SYNTHESIS (CHEMICAL);

PALLADIUM COMPOUNDS;

1,3 DIENE DERIVATIVE; ACETIC ACID DERIVATIVE; ALKADIENE; DIHYDROBENZOFURAN DERIVATIVE; IODIDE; OXYGEN; PALLADIUM COMPLEX; PHENOL; REDOX EFFECTOR FACTOR 1; UNCLASSIFIED DRUG;

ADDITION REACTION; ANNULATION REACTION; ARTICLE; CATALYSIS; CATALYST; ELECTRON; ELIMINATION REACTION; HYDROLYSIS; STEREOCHEMISTRY; SYNTHESIS;

ACETATES; ALKADIENES; BENZOFURANS; CATALYSIS; IODINE; MOLECULAR STRUCTURE; PALLADIUM;

EID: 77953496873     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100495t     Document Type: Article

References (35)

1. Dean, F. M. The Total Synthesis of Natural Products; ApSimon, J., Ed.; Wiley: New York, 1973; Vol. 1, p 513.
2. Li, S. Y.; Fuchino, H.; Kawahara, N.; Sekita, S.; Satake, M. J. Nat. Prod. 2002, 65, 262
3. Chen, C.-H.; Shaw, C.-Y.; Chen, C.-C.; Tsai, Y.-C. J. Nat. Prod. 2002, 65, 740
4. Yamaguchi, S.; Muro, S.; Kobayashi, M.; Miyazawa, M.; Hirai, Y. J. Org. Chem. 2003, 68, 6274
5. Bose, J. S.; Gangan, V.; Prakash, R.; Jain, S. K.; Manna, S. K. J. Med. Chem. 2009, 52, 3184
6. Kazuhiro, C.; Fukuda, M.; Shokaku, K.; Kitano, Y.; Talda, M. J. Org. Chem. 1999, 64, 7654
7. Entel, J.; Ruof, C. H.; Howard, H. C. J. Am. Chem. Soc. 1951, 73, 2365
8. Benbow, J. W.; Katoch-Rouse, R. J. Org. Chem. 2001, 66, 4965
9. Bakke, J. M.; Roholdt, H. M. Acta Chem. Scand., Ser. B. 1980, B34, 73
10. Inoue, K.; Sawada, A.; Shibata, I.; Baba, A. J. Am. Chem. Soc. 2002, 124, 906
11. Vaillard, S. E.; Postigo, A.; Rossi, R. A. J. Org. Chem. 2004, 69, 2037
12. Uozumi, Y.; Kyouta, H.; Kishi, E.; Kitayama, K.; Hayashi, T. Tetrahedron 1996, 6, 1603
13. Hayashi, T. J. Am. Chem. Soc. 1997, 119, 5063
14. Thalji, R. K.; Ahrendt, K. A.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 9692
15. Kuwabe, S.; Torraca, K. E.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 12202
16. Pelly, S. C.; Govender, S.; Fernandes, M. A.; Schmalz, H.-G.; de Koning, C. B. J. Org. Chem. 2007, 72, 2857
17. Tsuji, J. Palladium Reagents and Catalysts; J. Wiley & Sons: New York, 1995.
18. Posner, G. H. Chem. Rev. 1986, 86, 831
19. Trost, B. M. Chem. Soc. Rev. 1982, 11, 141
20. Larock, R. C. J. Organomet. Chem. 1999, 576, 111
21. Zeni, G.; Larock, R. C. Chem. Rev. 2004, 104, 2285
22. Zeni, G.; Larock, R. C. Chem. Rev. 2006, 106, 4644
23. Zeni, G.; Larock, R. C. Chem. Rev. 2007, 107, 303
24. Larock, R. C.; Guo, L. Synlett 1995, 465
25. Gagnier, S. V.; Larock, R. C. J. Org. Chem. 2000, 65, 1525
26. Larock, R. C.; Berrios-Peña, N.; Narayanan, K. J. Org. Chem. 1990, 55, 3447
27. Berrios-Peña, N.; Larock, R. C. Unpublished results.
28. Rozhkov, R. V.; Larock, R. C. Org. Lett. 2003, 5, 797
29. Rozhkov, R. V.; Larock, R. C. J. Org. Chem. 2003, 68, 6314
30. Rozhkov, R. V.; Larock, R. C. Tetrahedron Lett. 2004, 45, 911
31. Rozhkov, R. V.; Larock, R. C. Adv. Synth. Catal. 2005, 346, 1854
32. Heck, R. F. Org. React. 1982, 27, 345
33. Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314
34. Karabelas, K.; Westerlund, C.; Hallberg, A. J. Org. Chem. 1985, 50, 3896
35. Grigg, R.; Loganathan, V.; Santhakumar, V.; Sridrahan, V.; Teasdale, A. Tetrahedron Lett. 1991, 32, 687