Palladium-catalyzed aromatic C-H halogenation with hydrogen halides by means of electrochemical oxidation

Journal of the American Chemical Society

Volumn 131, Issue 32, 2009, Pages 11310-11311

  Kakiuchi, Fumitoshi ^a   Kochi, Takuya ^a   Mutsutani, Hitoshi ^a   Kobayashi, Noboru ^a   Urano, Seiya ^a   Sato, Mitsuo ^a   Nishiyama, Shigeru ^a   Tanabe, Takamasa ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

C-H BOND; C-H BOND CLEAVAGE; CATALYTIC ACTIVITY; CATALYTIC FUNCTIONALIZATION; CHEMICAL EQUATIONS; ELECTROCHEMICAL METHODS; HALONIUM; HYDROGEN HALIDES; NEW STRATEGY;

AROMATIC COMPOUNDS; CATALYTIC OXIDATION; CHEMICAL BONDS; ELECTROCHEMICAL CELLS; HALOGENATION; HYDROGEN; ORGANIC SOLVENTS; PALLADIUM;

ELECTROCHEMICAL OXIDATION;

AROMATIC COMPOUND; CARBON; CHLORINE; HALIDE; HYDROGEN; ORGANIC SOLVENT; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON;

AQUEOUS SOLUTION; ARTICLE; BROMINATION; CATALYSIS; CATALYST; CHLORINATION; CONTROLLED STUDY; DISSOCIATION; ELECTROCHEMISTRY; HALOGENATION; HYDROGEN BOND; MOLECULAR INTERACTION; OXIDATION; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 68849122353     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9049228     Document Type: Article

References (32)

1. (a) Trost, B. M. Science 1991, 254, 1471-1477.
2. (b) Charette, A. B. Nature 2008, 456, 451-453.
3. (a) Bergman, R. G. Nature 2007, 446, 391-393.
4. (b) Kakiuchi, F.; Kochi, T. Synthesis 2008, 3013-3039.
5. Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826-834.
6. Chen, H.; Schlecht, S.; Semple, T. C.; Hartwig, J. F. Science 2000, 287, 1995-1997.
7. (a) Dick, A. R.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 2300-2301.
8. (b) Kalyani, D.; Dick, A. R.; Anani, W. Q.; Sanford, M. S. Tetrahedron 2006, 62, 11483-11498.
9. (c) Kalyani, D.; Dick, A. R.; Anani, W. Q.; Sanford, M. S. Org. Lett. 2006, 8, 2523-2526.
10. (a) Kodama, H.; Katsuhira, T.; Nishida, T.; Hino, T.; Tsubata, K. Patent WO 2001083421 A1, 2001; Chem. Abstr. 2001, 135, 344284.
11. (b) Giri, R.; Chen, X.; Yu, J.-Q. Angew. Chem., Int. Ed. 2005, 44, 2112-2115.
12. (c) Hull, K. L.; Anani, W. Q.; Sanford, M. S. J. Am. Chem. Soc. 2006, 128, 7134-7135.
13. (d) Mei, T.-S.; Giri, R.; Maugel, N.; Yu, J.-Q. Angew. Chem., Int. Ed. 2008, 47, 5215-5219.
14. (a) Chen, X.; Hao, X.-S.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 6790-6791.
15. (b) Wan, X.; Ma, Z.; Li, B.; Zhang, K.; Cao, S.; Zhang, S.; Shi, Z. J. Am. Chem. Soc. 2006, 128, 7416-7417.
16. (c) Zhao, X.; Dimitrijević, E.; Dong, V. M. J. Am. Chem. Soc. 2009, 131, 3466-3467.
17. (a) Kalyani, D.; Sanford, M. Top. Organomet. Chem. 2007, 24, 85-116.
18. (b) Tsang, W. C. P.; Zheng, N.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 14560-14561.
19. (c) Thu, H.-Y.; Yu, W.-Y.; Che, C.-M. J. Am. Chem. Soc. 2006, 128, 9048-9049.
20. (d) Kim, S. H.; Lee, H. S.; Kim, S. H.; Kim, J. N. Tetrahedron Lett. 2008, 49, 5863-5866.
21. (a) Stuart, D. R.; Fagnou, K. Science 2007, 316, 1172-1175.
22. (b) Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2007, 129, 11904-11905.
23. (a) Yoshida, J.; Kataoka, K.; Horcajada, R.; Nagaki, A. Chem. Rev. 2008, 108, 2265-2299.
24. (b) Jutand, A. Chem. Rev. 2008, 108, 2300-2347.
25. Electrochemical oxidation of external oxidants in palladium catalysis has been reported: (a) Bäckvall, J.-E.; Gogoll, A. J. Chem. Soc., Chem. Commun. 1987, 1236-1238.
26. (b) Inokuchi, T.; Ping, L.; Hamaue, F.; Izawa, M.; Torii, S. Chem. Lett. 1994, 23, 121-124.
27. (c) Amatore, C.; Cammoun, C.; Jutand, A. Adv. Synth. Catal. 2007, 349, 292-296.
28. (d) Mitsudo, K.; Kaide, T.; Nakamoto, E.; Yoshida, K.; Tanaka, H. J. Am. Chem. Soc. 2007, 129, 2246-2247.
29. See the Supporting Information for the detailed experimental procedure.
30. (a) Horcajada, R.; Okajima, M.; Suga, S.; Yoshida, J. Chem. Commun. 2005, 1303-1305.
31. (b) Tajima, T.; Fuchigami, T. J. Am. Chem. Soc. 2005, 127, 2848-2849.
32. The structures of 20 and 22 were confirmed by X-ray crystallography (see the Supporting Information).