The first intramolecular Heck-Matsuda reaction and its application in the syntheses of benzofurans and indoles

Tetrahedron Letters

Volumn 51, Issue 16, 2010, Pages 2102-2105

  Siqueira, Fernanda A ^a   Taylor, Jason G ^a   Correia, Carlos Roque D ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOFURAN DERIVATIVE; DIHYDROBENZOFURAN ACETIC ACID DERIVATIVE; INDOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBONYLATION; CYCLIZATION; HECK REACTION; REACTION ANALYSIS; SYNTHESIS;

EID: 77949490972     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.02.011     Document Type: Article

References (42)

1. For selected reviews, see:. Shibasaki M., Vogl E.M., and Ohshima T. Adv. Synth. Catal. 346 (2004) 1533
2. Negishi E.-i., Copéret C., Ma S., Liou S., and Liu F. Chem. Rev. 96 (1996) 365
3. Dounai A.B., and Overman L.E. Chem. Rev. 103 (2003) 2945
4. Sato Y., Sodeoka M., and Shibasaki M. J. Org. Chem. 54 (1989) 4738
5. Carpenter N.E., Kucera D.J., and Overman L.E. J. Org. Chem. 54 (1989) 5846
6. Link J.T. Org. React. 60 (2002) 157
7. For reports on intramolecular Heck coupling reactions of aryl bromides, see:. Michael J.P., Chang S.F., and Wilson C. Tetrahedron Lett. 34 (1993) 8365
8. Pigeon P., and Decroix B. Tetrahedron Lett. 37 (1996) 7707
9. Mamouni A., Daïch A., and Decroix B. Synth. Commun. 28 (1998) 1839
10. Kiewel K., Tallant M., and Sulikpwski G.A. Tetrahedron Lett. 42 (2001) 6621
11. Cacchi S., and Fabrizi G. Chem. Rev. 105 (2005) 2873
12. For reports on intramolecular Heck coupling reactions of aryl iodides, see:. Joseph B., Cornec O., and Mérour J.-Y. Tetrahedron 54 (1998) 7765
13. Huang Q., Fazio A., Dai G., Campo M.A., and Larock R.C. J. Am. Chem. Soc. 126 (2004) 7460
14. Arnold L.A., Luo W., and Guy R.K. Org. Lett. 6 (2004) 3005
15. Majumdar K.C., Chattopadyay B., and Nath S. Tetrahedron Lett. 49 (2008) 1609
16. For precedents on indole synthesis by intramolecular Heck coupling reactions, see:. Parsons P.J., Charles M.D., Harvey D.M., Sumoreeah L.R., Shell A., Spoors G., Gill A.L., and Smith S. Tetrahedron Lett. 42 (2001) 2209
17. Dajka-Halász B., Monsieurs K., Éliás O., Károlyházy L., Tapolcsányi P., Maes B.U.W., Riedl Z., Hajós G., Dommisse R.A., Lemière G.L.F., Kosmrlj J., and Mátyus P. Tetrahedron 60 (2004) 2283
18. Söderberg B.C.G., Hubbard J.W., Rector S.R., and O'Neil S.N. Tetrahedron 61 (2005) 3637
19. Putey A., Joucla L., Picot L., Besson T., and Joseph B. Tetrahedron 63 (2007) 867
20. Yun W., and Mohan R. Tetrahedron Lett. 40 (1996) 7189
21. Yamazaki K., Nakamura Y., and Kondo Y. J. Org. Chem. 68 (2003) 6011
22. For precendents on benzofuran synthesis by intramolecular Heck coupling reactions, see:. Xie X., Chen B., Lu J., Han J., She X., and Pan X. Tetrahedron Lett. 45 (2004) 6235
23. Larock R.C., and Stinn D.E. Tetrahedron Lett. 29 (1988) 4687
24. Beckwith A.L.J., and Meijis F.G. J. Chem. Soc., Chem. Commun. (1981) 136
25. Meijis G.F., and Beckwith A.L.J. J. Am. Chem. Soc. 108 (1986) 5890
26. Beckwith A.L.J., and Meijis G.F. J. Org. Chem. 52 (1987) 1922
27. Sengupta S., and Bhattacharyya S. Tetrahedron Lett. 42 (2001) 2035
28. Kikukawa K., Nagira K., Wada F., and Matsuda T. Tetrahedron 37 (1981) 31
29. Kikukawa K., and Matsuda T. Chem. Lett. (1977) 159
30. Garcia A.L.L., Carpes M.J.S., Oca A.C.B.M., dos Santos M.A.G., Santana C.C., and Correia C.R.D. J. Org. Chem. 70 (2005) 1050
31. Pastre J.C., and Correia C.R.D. Org. Lett. 8 (2006) 1657
32. Garcia A.L.L., and Correia C.R.D. Tetrahedron Lett. 44 (2003) 1553
33. Severino E.A., Costenaro E.R., Garcia A.L.L., and Correia C.R.D. Org. Lett. 5 (2003) 305
34. Machado A.H.L., Souza M.A., Patto D.S.C., Azevedo L.F.S., Bombonato F.I., and Correia C.R.D. Tetrahedron Lett. 50 (2009) 12222
35. Barnar C.F.J. Org. Process Res. Dev. 12 (2008) 566
36. Baldwin J.E. Chem. Commun. (1976) 734
37. Beletskaya I.P., and Cheprakov A.V. Chem. Rev. 100 (2000) 3009
38. Majumdar K.C., and Chattopadhyay B. Curr. Org. Chem. 13 (2009) 731
39. Gibson S.E., and Middleton R. J. Chem. Commun. 52 (1995) 1743
40. Leggy A.A., Wenchen L., and Guy R.K. Org. Lett. 6 (2004) 3005
41. A standard diazotisation methodology can be found in the Supplementary data: refer to arenediazonium salts 1, 5 and 7.
42. Confirmed by nuclear Overhauser enhancement (nOe) of the aromatic resonance when the olefinic proton was irradiated, that being the only resonance so affected.