K. Mori, T. Hara, T. Mizugaki, K. Ebitani and K. Kaneda, J. Am.
Notes and references
Chem. Soc., 2004, 126, 10657 and references therein.
3 R. A. Sheldon, I. W. C. E. Arends and A. Dijksman, Catal. Today,
2000, 57, 157.
{ Experimental. All alcohols and solvents were used as received without
any further purification. The oxidation of alcohols was carried out under
air in a 50 ml three-necked round-bottom flask equipped with a magnetic
stirrer. Typically, the alcohol (10.0 mmol) and TEMPO (0.5 mmol) were
dissolved in 10 ml trifluorotoluene. FeCl3?6H2O (0.5 mmol) was added
followed by NaNO2 (0.5 mmol). The resulting mixture was stirred at room
temperature and ambient pressure. The conversion and selectivity of the
reaction was detected by GC without any purification.
4 (a) F. M. Semmelhack, C. R. Schmidt, D. A. Cortes and C. S. Chou,
J. Am. Chem. Soc., 1984, 106, 3374; (b) B. Betzemeier, M. Cavazzini,
S. Quici and P. Knochel, Tetrahedron Lett., 2000, 41, 4343; (c)
A. Cecchetto, F. Fontana, F. Minisci and F. Recupero, Tetrahedron
Lett., 2001, 42, 6651; (d) A. Dijksman, A. Mmarino-Gonzalez,
A. Mairata, I. Payeras, I. W. C. E. Arends and R. A. Sheldon, J. Am.
Chem. Soc., 2001, 123, 6826; (e) R. Ben-Daniel, P. Alsters and
R. Neumann, J. Org. Chem., 2001, 66, 8650; (f) I. A. Ansari and
R. Gree, Org. Lett., 2002, 4, 1507; (g) P. Gamez, I. W. C. E. Arends,
J. Reedijk and R. A. Sheldon, Chem. Commun., 2003, 2414.
5 R. Liu, X. Liang, C. Dong and X. Hu, J. Am. Chem. Soc., 2004, 126,
4112.
6 F. A. Cotton, G. Wilkinson, B. Manfred and M. Carlos, Advanced
Inorganic Chemistry, 6th edn.; Wiley: New York, 1998, pp 796–808.
7 I. M. Wasser, S. D. Vries, P. Moe¨nne-Loccoz, I. Schro¨der and
K. D. Karlin, Chem. Rev., 2002, 102, 1201.
8 S. E. Martin and D. F. Suarez, Tetrahedron lett., 2002, 43, 4475.
9 (a) J. Laugier, J.-M. Latour, A. Caneschi and P. Rey, Inorg. Chem.,
1991, 30, 4474; (b) A. Dijksman, I. W. C. E. Arends and R. A. Sheldon,
Org. Biomol. Chem., 2003, 1, 3232.
1 M. Hudlicky, Oxidations in Organic Chemistry, American Chemical
Society, Washington, DC, 1990.
2 (a) G.-J. ten Brink, I. W. C. E. Arends and R. A. Sheldon, Science,
2000, 287, 1636; (b) S. S. Stahl, J. L. Thorman, R. C. Nelson and
M. A. Kozee, J. Am. Chem. Soc., 2001, 123, 7188; (c) B. A. Steinhoff,
S. R. Fix and S. S. Stahl, J. Am. Chem. Soc., 2002, 124, 766; (d)
J. Muldoon and S. N. Brown, Org. Lett., 2002, 4, 1043; (e)
K. Yamaguchi and N. Mizuno, Angew. Chem., Int. Ed., 2002, 41,
4538; (f) M. J. Schultz, C. C. Park and M. S. Sigman, Chem. Commun.,
2002, 3034; (g) Y. Uozumi and R. Nakao, Angew. Chem., Int. Ed., 2003,
42, 194; (h) B.-Z. Zhan, M. A. White, T.-K. Sham, J. A. Pincock,
R. J. Doucet, K. V. Ramana Rao, K. N. Robertson and T. S. Cameron,
J. Am. Chem. Soc., 2003, 125, 2195; (i) D. R. Jensen, M. J. Schultz,
J. A. Mueller and M. S. Sigman, Angew. Chem., Int. Ed., 2003, 42, 3810;
(j) I. E. Marko, A. Gautier, R. L. Dumeunier, K. Doda, F. Philippart,
S. M. Brown and C. J. Urch, Angew. Chem., Int. Ed., 2004, 43, 1588; (k)
10 I. R. Epstein, K. Kustin and L. J. Warshaw, J. Am. Chem. Soc., 1980,
102, 3751.
11 P. Bar-on, M. Mohsen, R. Zhang, E. Feigin, M. Chevion and
A. Samuni, J. Am. Chem. Soc., 1999, 121, 8070.
5324 | Chem. Commun., 2005, 5322–5324
This journal is ß The Royal Society of Chemistry 2005