Oxidative homo-coupling of potassium aryltrifluoroborates catalyzed by gold nanocluster under aerobic conditions

Journal of Organometallic Chemistry

Volumn 692, Issue 1-3, 2007, Pages 368-374

  Sakurai, Hidehiro ^a   Tsunoyama, Hironori ^a   Tsukuda, Tatsuya ^a,b  

^a INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

Aerobic oxidation; Aryltrifluoroborate; Gold nanocluster; Homo coupling

Indexed keywords

CATALYSIS; GOLD; NANOSTRUCTURED MATERIALS; ORGANOMETALLICS; OXIDATION; REACTION KINETICS;

AEROBIC OXIDATION; ARYLTRIFLUOROBORATE; GOLD NANOCLUSTERS; HOMOCOUPLING;

POTASSIUM COMPOUNDS;

EID: 33845633975     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2006.04.054     Document Type: Article

References (48)

1. Haruta M., Yamada N., Kobayashi T., and Iijima S. J. Catal. 115 (1989) 301
2. Haruta M. Nature 437 (2005) 1098
3. Schmid G., and Corain B. Eur. J. Inorg. Chem. (2003) 3081
4. Enache D.I., Edwards J.K., Landon P., Solsona-Espriu B., Carley A.F., Herzing A.A., Watanabe M., Kiely C.J., Knight D.W., and Hutchings G.J. Science 311 (2006) 362
5. Astruc D., Lu F., and Aranzaes J.R. Angew. Chem., Int. Ed. 44 (2005) 7852
6. Tsunoyama H., Sakurai H., Ichikuni N., Negishi Y., and Tsukuda T. Langmuir 20 (2004) 11293
7. Tsunoyama H., Sakurai H., Negishi Y., and Tsukuda T. J. Am. Chem. Soc. 127 (2005) 9374
8. Tsunoyama H., Sakurai H., and Tsukuda T. Chem. Phys. Lett. 429 (2006) 528
9. Sakurai H., Tsunoyama H., and Tsukuda T. Trans. Mater. Res. Soc. Jpn. 31 (2006) 521
10. Moreno-Mañas M., Pérez M., and Pleixats R. J. Org. Chem. 61 (1996) 2346
11. Hata H., Shinokubo H., and Osuka A. J. Am. Chem. Soc. 127 (2005) 8264
12. Smith K.A., Campi E.M., Jackson W.R., Marcuccio S., Naeslund C.G.M., and Deacon G.B. Synlett (1997) 131
13. Wang M.S., and Zhang X.L. Tetrahedron Lett. 42 (2001) 4087
14. Perrish J.P., Jung Y.C., Floyd R.J., and Jung K.W. Tetrahedron Lett. 43 (2002) 7899
15. Yoshida H., Yamaryo Y., Ohshita J., and Kunai A. Tetrahedron Lett. 44 (2003) 1541
16. Punna S., Díaz D.D., and Finn M.G. Synlett (2004) 2351
17. Demir A.S., Reis O., and Emrullahoglu M. J. Org. Chem. 68 (2003) 10130
18. Demir A.S., Reis O., and Emrullahoglu M. J. Org. Chem. 68 (2003) 578
19. Carrettin S., Guzman J., and Corma A. Angew. Chem., Int. Ed. 44 (2005) 2242
20. González-Arellano C., Corma A., Iglesias M., and Sánchez F. Chem. Commun. (2005) 1990
21. Vedejs E., Chapman R.W., Fields S.C., Lin S., and Schrimpf M.R. J. Org. Chem. 60 (1995) 3020
22. Pelter A., Smith K., and Brown H.C. Borane Reagents (1988), Academic Press, London
23. Molander G.A., and Biolatto B. Org. Lett. 4 (2002) 1867
24. Molander G.A., and Biolatto B. J. Org. Chem. 68 (2003) 4302
25. Batey R.A., and Quach T.D. Tetrahedron Lett. 42 (2001) 9099
26. Darses S., Genêt J.-P., Brayer J.-L., and Demoute J.-P. Tetrahedron Lett. 38 (1997) 4393
27. Chen Z.-C., and Xia M. Synth. Commun. 29 (1999) 2457
28. 3K and m-iodophenol in pH 6.86 buffer was treated with Au:PVP-1, cross-coupling product, m-hydroxybiphenyl, was not detected but homo-coupling product, biphenyl, was obtained as a sole product. Details of such competitive reactions will be described elsewhere.
29. Li Y., Hong X.M., Collard D.M., and El-Sayed M.A. Org. Lett. 2 (2000) 2385
30. Li Y., Boone E., and El-Sayed M.A. Langmuir 18 (2002) 4921
31. Narayanan R., and El-Sayed M.A. J. Am. Chem. Soc. 125 (2002) 8340
32. Narayanan R., and El-Sayed M.A. J. Phys. Chem. B 108 (2004) 8572
33. Sakurai H., Hirao T., Negishi Y., Tsunakawa H., and Tsukuda T. Trans. Mater. Res. Soc. Jpn. 27 (2002) 185
34. Guan B., Xing D., Cai G., Wan X., Yu N., Fang Z., Yang L., and Shi Z. J. Am. Chem. Soc. 127 (2005) 18004
35. González-Arellano C., Corma A., Iglesias M., and Sánchez F. J. Catal. 238 (2006) 497
36. Reetz M.T., and de Vries J.G. Chem. Commun. (2004) 1559
37. Thathagar M.B., Kooyman P.J., Boerleider R., Jansen E., Elsevier C.J., and Rothenberg G. Adv. Synth. Catal. 347 (2005) 1965
38. Henglein A. Langmuir 15 (1999) 6738
39. Salisburry B.E., Wallace W.T., and Whetten R.L. Chem. Phys. 262 (2000) 131
40. Okumura M., Kitagawa Y., Haruta M., and Yamaguchi K. Chem. Phys. Lett. 346 (2001) 163
41. Wells Jr. D.H., Delgass W.N., and Thomson K.T. J. Chem. Phys. 117 (2002) 10597
42. Yoon B., Häkkinen H., and Landman U. J. Phys. Chem. A 107 (2003) 4066
43. Stolcic D., Fischer M., Ganteför G., Kim Y.D., Sun Q., and Jena P. J. Am. Chem. Soc. 125 (2003) 2848
44. Stiehl J.D., Kim T.S., McClure S.M., and Mullins C.B. J. Am. Chem. Soc. 126 (2004) 1606
45. Bongiorno A., and Landman U. Phys. Rev. Lett. 95 (2005) 106102
46. Suzaki Y., and Osakada K. Bull. Chem. Soc. Jpn. 77 (2004) 139
47. Suzaki Y., and Osakada K. Organometallics 23 (2004) 5081
48. Ionita P., Gilbert B.C., and Chechik V. Angew. Chem., Int. Ed. 44 (2005) 3720