Synthesis of benzo[c]chromen-6-ones via novel cyclic aryl-Pd(II)-ester enolate intermediates

Tetrahedron

Volumn 63, Issue 45, 2007, Pages 10889-10895

  Taylor, Stephen R ^a   Ung, Alison T ^a   Pyne, Stephen G ^a  

^a UNIVERSITY OF WOLLONGONG   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

BENZO[C]CHROMEN 6 ONE; BENZOIC ACID; CARBON; CINNAMIC ACID DERIVATIVE; DEHYDROCINNAMIC ACID; HYDROGEN; PALLADIUM; PHENYLACETIC ACID; SUCCINIC ACID; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CATALYSIS; PRIORITY JOURNAL; SYNTHESIS;

EID: 34648832247     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.08.080     Document Type: Article

References (40)

1. See for example:
2. Ames D.E., and Opalko A. Tetrahedron 40 (1984) 1919-1925
3. Deshpande P.P., and Martin O.R. Tetrahedron Lett. 31 (1990) 6313-6316
4. Hosoya T., Takashiro E., Matsumoto T., and Suzuki E. J. Am. Chem. Soc. 116 (1994) 1004-1015
5. Qabaja G., and Jones G.B. J. Org. Chem. 65 (2000) 7187-7194
6. Bringmann G., and Menche D. Acc. Chem. Res. 34 (2001) 615-624
7. Bringmann G., Menche D., Muhlbacher J., Reichert M., Saito N., Pfeiffer S.S., and Lipshutz B. Org. Lett. 4 (2002) 2833-2836
8. Molander G.A., George K.M., and Monovich L.G. J. Org. Chem. 68 (2003) 9533-9540
9. Abe H., Takeda S., Fujita T., Nishioka K., Takeuchi Y., and Harayama T. Tetrahedron Lett. 45 (2004) 2327-2329
10. Abe H., Nishioka K., Takeda S., Arai M., Takeuchi Y., and Harayama T. Tetrahedron Lett. 46 (2005) 3197-3200
11. Cordero-Vargas A., Quiclet-Sire B., and Zard S.Z. Org. Biomol. Chem. 3 (2005) 4432-4443
12. For the synthesis of the corresponding lactams, see:
13. Harayama T., Kawata Y., Nagura C., Sata T., Miyagoe T., Abe H., and Takeuchi Y. Tetrahedron Lett. 46 (2005) 6091-6094
14. Harayama T., Hori A., Abe H., and Takeuchi Y. Heterocycles 67 (2006) 385-390
15. Campeau L.-C., Parisien M., Jean A., and Fagnou K. J. Am. Chem. Soc. 128 (2006) 581-590
16. Campeau L.-C., and Fagnou K. Chem. Commun. (2006) 1253-1264
17. Dyker G. Angew. Chem., Int. Ed. 38 (1999) 1699-1712
18. Larock R.C., Doty M.J., and Cacchi S. J. Org. Chem. 58 (1993) 4579-4583
19. Campo M.A., Huang Q., Yao T., Tian Q., and Larock R.C. J. Am. Chem. Soc. 125 (2003) 11506-11507
20. Huang Q., Fazio A., Dai G., Campo M.A., and Larock R.C. J. Am. Chem. Soc. 126 (2004) 7460-7461
21. Huang Q., Campo M.A., Yao T., Tian Q., and Larock R.C. J. Org. Chem. 69 (2004) 8251-8257
22. Torres J.C., Pinto A.C., and Garden S.J. Tetrahedron 60 (2004) 9889-9900
23. Ma S., and Gu Z. Angew. Chem., Int. Ed. 44 (2005) 7512-7517
24. Zhao J., Campo M., and Larock R.C. Angew. Chem., Int. Ed. 44 (2005) 1873-1875
25. Barder T.E., Walker S.D., Martinelli J.R., and Buchwald S.L. J. Am. Chem. Soc. 127 (2005) 4685-4696
26. Zhao J., and Larock R.C. Org. Lett. 7 (2005) 701-704
27. Zhao J., and Larock R.C. J. Org. Chem. 71 (2006) 5340-5348
28. Zhou C., and Larock R.C. J. Org. Chem. 71 (2006) 3551-3558
29. Chen X., Goodhue C.E., and Yu J.-Q. J. Am. Chem. Soc. 128 (2006) 12634-12635
30. Mota A.J., and Dedieu A. Organometallics 25 (2006) 3130-3142
31. Zhao J., Yue D., Campo M.A., and Larock R.C. J. Am. Chem. Soc. 129 (2007) 5288-5295
32. Campo M.A., Zhang H., Yao T., Ibday A., McCulla R.D., Huang Q., Zhao J., Jenks W.S., and Larock R.C. J. Am. Chem. Soc. 129 (2007) 6298-6307
33. Churruca F., SanMartin R., Tellitu I., and Dominguez E. Eur. J. Org. Chem. (2005) 2481-2490
34. Willis M.C., Taylor D., and Gillmore A.T. Org. Lett. 6 (2004) 4755-4757
35. Terao Y., Satoh T., Miura M., and Nomura M. Bull. Chem. Soc. Jpn. 72 (1999) 2345-2350
36. We thank a referee for drawing this possibility to our attention.
37. Fox J.M., Huang X., Chieffi A., and Buchwald S.L. J. Am. Chem. Soc. 122 (2000) 1360-1370
38. Culkin D.A., and Hartwig J.F. Acc. Chem. Res. 36 (2003) 234-245
39. Beugelmans R., Bois-Choussy M., Chastanet J., Le Gleuher M., and Zhu J. Heterocycles 36 (1993) 2723-2732
40. Cheetham, P.; Samual, J.; Bannister, N. E. PCT Int. Appl. WO 95 GB132519950607, 1995.