Copper-catalysed benzofuran synthesis: developing aryl bromide-alkenyl triflates as general heterocycle precursors

Tetrahedron Letters

Volumn 48, Issue 43, 2007, Pages 7578-7581

  Tadd, Andrew C ^a   Fielding, Mark R ^b   Willis, Michael C ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOFURAN DERIVATIVE; BROMIDE ALKENYL TRIFLATE; BROMINE DERIVATIVE; COPPER; POTASSIUM HYDROXIDE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 34548830666     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.08.109     Document Type: Article

References (27)

1. Pozharskii F., Soldatenkov A.T., and Katritzky A.R. Heterocycles in Life and Society (1997), Wiley, Chichester
2. Gilchrist T.L. J. Chem. Soc., Perkin Trans. 1 (2001) 2491
3. In: Katritzky A.R., and Rees C.W. (Eds). Comprehensive Heterocyclic Chemistry Vol. 1 (1984), Pergamon Press, New York
4. Willis M.C., Brace G.N., Findlay T.J.K., and Holmes I.P. Adv. Synth. Catal. 348 (2006) 851
5. Willis M.C., Brace G.N., and Holmes I.P. Angew. Chem., Int. Ed. 44 (2005) 403
6. Mann G., Incarvito C., Rheingold A.L., and Hartwig J.F. J. Am. Chem. Soc. 121 (1999) 3224
7. Kataoka N., Shelby Q., Stambuli J.P., and Hartwig J.F. J. Org. Chem. 67 (2002) 5553
8. Anderson K.W., Ikawa T., Tundel R.E., and Buchwald S.L. J. Am. Chem. Soc. 128 (2006) 10694
9. For a highlight article, see:. Willis M.C. Angew. Chem., Int. Ed. 46 (2007) 3402
10. For general reviews on Palladium in heterocycle synthesis, see:. Li J.J., and Gribble G.W. Palladium in Heterocyclic Chemistry. 2nd ed. (2007), Elsevier, Oxford
11. Nakamura I., and Yamamoto Y. Chem. Rev. 104 (2004) 2127
12. Zeni G., and Larock R.C. Chem. Rev. 106 (2006) 4644
13. For examples of recent benzofuran syntheses that deliver 2,3-substituted products, see:. Takeda N., Miyata O., and Naito T. Eur. J. Org. Chem. (2007) 1491
14. Bernini R., Cacchi S., De Salve I., and Fabrizi G. Synthesis (2007) 873
15. Zhao B., and Lu X. Org. Lett. 8 (2006) 5987
16. Sanz R., Miguel D., Martínez A., and Pérez A. J. Org. Chem. 71 (2006) 4024
17. Yue D.W., Yao T.L., and Larock R.C. J. Org. Chem. 70 (2005) 10292
18. tBu-X-phos, Xantphos, DPEphos.
19. For intramolecular Pd enolate O-arylations, see:. Terao Y., Satoh T., Miura M., and Nomura M. Bull. Chem. Soc. Jpn. 72 (1999) 2345
20. Willis M.C., Taylor D., and Gillmore A.T. Org. Lett. 6 (2004) 4755
21. Churruca F., SanMartin R., Tellitu I., and Domínguez E. Eur. J. Org. Chem. (2005) 2481
22. Willis M.C., Taylor D., and Gillmore A.T. Tetrahedron 62 (2006) 11513
23. For a recent review on Cu-catalysed C-X bond formation, see:. Ley S.V., and Thomas A.W. Angew. Chem., Int. Ed. 42 (2003) 5400
24. Carril M., SanMartin R., Tellitu I., and Domínguez E. Org. Lett. 8 (2006) 1467
25. For a similar Cu-catalysed cyclisation, see:. Chen C.-Y., and Dormer P.G. J. Org. Chem. 70 (2005) 6964
26. 10b
27. 4S requires 449.9543).