Electrochemical recycling of benzoquinone in the Pd/benzoqui-none-catalyzed heck-type reactions from arenes

Advanced Synthesis and Catalysis

Volumn 349, Issue 3, 2007, Pages 292-296

  Amatore, Christian ^a   Cammoun, Chama ^a   Jutand, Anny ^a  

^a ECOLE NORMALE SUPÉRIEURE   (France)

Author keywords

Arenes; Benzoquinone; Catalysis; Electrochemistry; Hydroquinone; Palladium

Indexed keywords

EID: 34547174117     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200600389     Document Type: Article

References (19)

1. a) R. F. Heck, J. Am Chem. Soc. 1968, 90, 5538-5542;
2. b) A. de Meijere, F. E. Meyer, Angew. Chem. Int. Ed. Engl. 1994, 33, 2379-2411;
3. c) I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009-3066;
4. d) M. Larhed, A. Hallberg, Handbook of Organopalladium Chemistry for Organic Synthesis, (Ed.: E. Negishi), Wiley-Interscience, New-York, 2002, Vol. I, Chapter IV.2, pp. 1133-1178;
5. e) V. Farina, Adv. Synth. Catal 2004, 346, 1553-1582.
6. a) M. Dams, D.E. De Vos; S. Celen, P.A. Jakobs, Angew. Chem. Int. Ed. 2003, 42, 3512-3515;
7. b) C. Jia, T. Kitamura, Y. Fujiwara, Acc. Chem. Res. 2001, 34, 633-639;
8. c) C. Jia, Y. Fujiwara, Pure Appl. Chem. 2001, 73, 319-324, and references cited therein.
9. M. D. K. Boele, G. P. F. van Strijdonck, A. H. M. de V-ries, P. C. J. Kamer, J. G. de Vries, P. W. N. M. van Leeu-wen, J. Am. Chem. Soc. 2002, 124, 1586-1587.
10. For reviews on orthometallation, see: a) A. D. Ryabov, Chem. Rev. 1990, 90, 403-424;
11. b) M. Pfeffer, Pure Appl. Chem. 1992, 64, 335-342;
12. c) S. Tsuji, Palladium Reagents and Catalysis, John Wiley & Sons, Chichester, 1995.
13. C. Jia, W. Lu, T. Kitamura, Y. Fujiwara, Org. Lett. 1999, 1, 2097-2100.
14. J.-E. Bäckvall, A. Gogoll, J. Chem. Soc, Chem. Commun. 1987, 1236-1238.
15. H. Horino, N. Inoue, J. Org. Chem. 1981, 46, 4416-4422.
16. E. Capito, J. M. Brown, A. Ricci, Chem. Commun 2005, 1854-1856.
17. For other roles of the base in Heck reactions, see: C. Amatore, A. Jutand, Acc. Chem. Res. 2000, 33, 314-321.
18. C. Amatore, A. Jutand, G. Meyer, I. Carelli, I. Chiarot-to, Eur. J. Inorg. Chem. 2000, 1855-1859.
19. J.-E. Bäckvall, Pure Appl. Chem. 1992, 64, 429-437.