Facile synthesis of 2,3-dihydrobenzofuran-3-ylacetic acids by novel electrochemical sequential aryl radical cyclization-carboxylation of 2-allyloxybromobenzenes using methyl 4-tert-butylbenzoate as an electron-transfer mediator

Synlett

Volumn , Issue 11, 2011, Pages 1567-1572

  Senboku, Hisanori ^a   Michinishi, Jun Ya ^a   Hara, Shoji ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

2,3 dihydrobenzofuran 3 ylacetic acids; electrochemical reduction; fixation of carbon dioxide; radical cyclization; radical anion tandem reaction

Indexed keywords

2 ALLYLOXYBROMOBENZENE DERIVATIVE; 2,3 DIHYDROBENZOFURAN 3 YLACETIC ACID DERIVATIVE; ACETIC ACID DERIVATIVE; BENZENE DERIVATIVE; BENZOIC ACID DERIVATIVE; METHYL 4 TERT BUTYLBENZOATE; UNCLASSIFIED DRUG;

ARTICLE; CARBOXYLATION; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; CYCLIZATION; ELECTROCHEMISTRY; ELECTROLYSIS; ELECTRON TRANSPORT; NUCLEOPHILICITY; PROTON NUCLEAR MAGNETIC RESONANCE; PURIFICATION; STEREOCHEMISTRY; SYNTHESIS; TEMPERATURE;

EID: 79959373196     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1260794     Document Type: Article

References (37)

1. Grimshaw J, Trocha-Grimshaw J, Tetrahedron Lett. 1974 15 993
2. Grimshaw J, Haslett R J., Trocha-Grimshaw J, J. Chem. Soc., Perkin Trans. 1 1977 2448
3. Grimshaw J, Mannus D, J. Chem. Soc., Perkin Trans. 1 1977 2456
4. Grimshaw J, Hamilton R, Trocha-Grimshaw J, J. Chem. Soc., Perkin Trans. 1 1982 229
5. Donnelly S, Grimshaw J, Trocha-Grimshaw J, [nl] J. Chem. Soc., Chem. Commun. 1994 2171
6. LeStrat F, Murphy J A., Hughes M, Org. Lett. 2002 4 2735
7. Ozaki S, Matsushita H, Ohmori H, J. Chem. Soc., Chem. Commun. 1992 1120
8. Ozaki S, Matsushita H, Ohmori H, J. Chem. Soc., Perkin Trans. 1 1993 2339
9. Ozaki S, Horiguchi J, Matsushita H, Ohmori H, Tetrahedron Lett. 1994 35 725
10. Ihara M, Katsumata A, Setsu F, Tokunaga Y, Fukumoto K, J. Org. Chem. 1996 61 677
11. Olivero S, Clinet J C., Duñach E, Tetrahedron Lett. 1995 36 4429
12. Clinet J C., Duñach E, J. Organomet. Chem. 1995 503 C48
13. Gómez M, Muller G, Penyella D, Rocamora M, Duñach E, Olivero S, Clinet J C., Organometallics 1997 16 5900
14. Olivero S, Rolland J P., Dunãch E, Organometallics 1998 17 3747
15. Torii S, Inokuchi T, Yukawa T, J. Org. Chem. 1985 50 5875
16. Inokuchi T, Kawafuchi H, Aoki K, Yoshida A, Torii S, Bull. Chem. Soc. Jpn. 1994 67 595
17. Munusamy R, Dhathathreyan K S., Balasubramanian [nl]K K., Venkatachalam C H., J. Chem. Soc., Perkin Trans. 2 2001 1154
18. Kurono N, Honda E, Komatsu F, Orito K, Tokuda M, Chem. Lett. 2003 32 720
19. Kurono N, Honda E, Komatsu F, Orito K, Tokuda M, Tetrahedron 2004 60 1791
20. th, 2010, Abstr. No. 818.
21. Molander G A., Harris C R., Chem. Rev. 1996 96 307
22. Representative papers:, Curran D P., Totleben M J., [nl] J. Am. Chem. Soc. 1992 114 6050
23. Molander G A., McKie J A., J. Org. Chem. 1992 57 3132
24. Nomoto A, Koji Y, Shiino G, Tomisaka Y, Mitani I, Tatsumi M, Ogawa A, Tetrahedron Lett. 2010 51 6580
25. Olivero S, Duñach E, Eur. J. Org. Chem. 1999 1885
26. Recent papers:, Senboku H, Yamauchi Y, Fukuhara T, Hara S, Electrochemistry 2006 74 612
27. Senboku H, Takahashi M, Fukuhara T, Hara S, Chem. Lett. 2007 36 228
28. Yamauchi Y, Fukuhara T, Hara S, Senboku H, Synlett 2008 438
29. Yamauchi Y, Sakai K, Fukuhara T, Hara S, Senboku H, Synthesis 2009 3375
30. Yamauchi Y, Hara S, Senboku H, Tetrahedron 2010 66 473
31. Senboku H, Nakahara K, Fukuhara T, Hara S, Tetrahedron Lett. 2010 51 435
32. Ohkoshi M, Michinishi J, Hara S, Senboku H, Tetrahedron 2010 66 7732
33. Maekawa H, Murakami T, Miyazaki T, Nishiguchi I, Chem. Lett. 2011 40 368; and references cited therein
34. Silvestri G, Gambino S, Filardo G, Gulotta A, Angew. Chem., Int. Ed. Engl. 1984 23 979
35. Silvestri G, Gambino S, Filardo G, Acta Chem. Scand. 1991 45 987
36. Sock O, Troupel M, Périchon J, Tetrahedron Lett. 1985 26 1509
37. Chaussard J, Folest J C., Nédélec J Y., Périchon J, Sibille S, Troupel M, Synthesis 1990 369