Pd-catalyzed direct arylation of 3-fluorofurans utilizing the neighboring effect of fluorine atom: facile synthesis of tetrasubstituted monofluoro furans

Tetrahedron

Volumn 65, Issue 8, 2009, Pages 1673-1678

  Li, Peng ^a   Chai, Zhuo ^a   Zhao, Gang ^a   Zhu, Shi Zheng ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Aryl bromide; Arylation; C H activation; Fluorinated furans; Neighboring effect

Indexed keywords

3 FLUOROFURAN DERIVATIVE; FLUORINE; FURAN DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CATALYSIS; PRIORITY JOURNAL; QUANTUM YIELD; REACTION ANALYSIS; REACTION OPTIMIZATION; SUBSTITUTION REACTION;

EID: 58249097449     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.12.026     Document Type: Article

References (29)

1. For reviews:
2. Lautens M., Scott M.E., and Alberico D. Chem. Rev. 107 (2007) 174
3. Seregin I.V., and Gevorgyan V. Chem. Soc. Rev. (2007) 1173
4. Lewis J.C., Bergman R.G., and Ellman J.A. Acc. Chem. Res. 41 (2008) 1013
5. For recent examples:
6. Chuprakov S., Chernyak N., Dudnik A.S., and Gevorgyan V. Org. Lett. 9 (2007) 2333
7. Lebrasseur N., and Larrosa L. J. Am. Chem. Soc. 130 (2008) 2926
8. Campeau L.-C., Rousseaux S., and Fagnou K. J. Am. Chem. Soc. 127 (2005) 18020
9. Bellina F., Benelli F., and Rossi R. J. Org. Chem. 73 (2008) 5529
10. Old D.W., Harris M.C., and Buchwald S.L. Org. Lett. 2 (2000) 1403
11. Hartwig J.F., Kawatsura M., Hauck S.I., Shaughnessy K.H., and Alcazar-Roman L.M. J. Org. Chem. 64 (1999) 5575
12. For recent examples:
13. Yanagisawa S., Sudo T., Noyori R., and Itami K. J. Am. Chem. Soc. 128 (2006) 11748
14. Campeau L.-C., Bertrand-Laperle M., Leclerc J.-P., Villemure E., Gorelsky S., and Fagnou K. J. Am. Chem. Soc. 130 (2008) 3276
15. Battace A., Lemhadri M., Zair T., Doucet H., and Santelli M. Adv. Synth. Catal. 349 (2007) 2507
16. Besselièvre F., Mahuteau-Betzer F., Grierson D.S., and Piguel S. J. Org. Chem. 72 (2007) 3278
17. Fujiwara Y., Maruyama O., Yoshidomi M., and Taniguchi H. J. Org. Chem. 46 (1981) 851
18. Arimitsu S., Jacobsen J.M., and Hammond G.B. J. Org. Chem. 73 (2008) 2886
19. Sham H.-L., and Betebenner D.-A. J. Chem. Soc., Chem. Commun. (1991) 1134
20. Arimitsu S., and Hammond G.B. J. Org. Chem. 72 (2007) 8559
21. Lafrance M., Rowley C.N., Woo T.K., and Fagnou K. J. Am. Chem. Soc. 128 (2006) 8754
22. Do H.-Q., and Daugulis O. J. Am. Chem. Soc. 130 (2008) 1128
23. Li P., Chai Z., Zhao G., and Zhu S.-Z. Synlett (2008) 2547
24. Ceylan M., Gürdere M.B., Budak Y., Kazaz V., and Seçen H. Synthesis 11 (2004) 1750
25. Amarnath V., and Amarnath K. J. Org. Chem. 60 (1995) 301
26. Chiong H.A., and Daugulis O. Org. Lett. 9 (2007) 1449
27. Park C.-H., Ryabova V., Seregin I.V., Sromek A.W., and Gevorgyan V. Org. Lett. 9 (2007) 2333
28. Lane B.S., Brown M.A., and Sames D. J. Am. Chem. Soc. 127 (2005) 8050
29. Gilchrist T.L. Heterocyclic Chemistry. 3rd ed. (1997), Addison Wesley Longman, London