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see: Wu, X.-F.; Neumann, H.; Beller, M. Chem. Soc. Rev. 2011, 40, 4986–5009.
For selected examples on the oxidation of benzyl substrates, see: (a)
Rothenberg, G.; Wiener, H.; Sasson, Y. J. Mol. Catal. A: Chem. 1998, 136, 253–
7
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10. Wu, X.-F. Chem. Asian J. 2012. doi: asia.201200596.
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12. General comments: All reactions were carried out under air. ZnBr ,
2
2
439–2445; (d) Dohi, T.; Takenaga, N.; Goto, A.; Fujioka, H.; Kita, Y. J. Org. Chem.
008, 73, 7365–7368; (e) Lee, N. H.; Lee, C.-S.; Jung, D.-S. Tetrahedron Lett. 1998,
trifluoroacetic acid, 1,4-dioxane, and all the substrates were purchased from
Aldrich or FluoroChem and used as received. Gas chromatography analysis was
performed on an Agilent HP-5890 instrument with a FID detector and HP-5
capillary column (polydimethylsiloxane with 5% phenyl groups, 30 m, 0.32 mm
i.d., 0.25 lm film thickness) using argon as carrier gas. Gas chromatography-
mass analysis was carried out on an Agilent HP-5890 instrument with an
Agilent HP-5973 Mass Selective Detector (EI) and HP-5 capillary column
3
(
4
(
9, 1385–1388; (f) Nagano, T.; Kobayashi, S. Chem. Lett. 2008, 37, 1042–1043;
g) Gonzalez, M. J.; Sullivan, A. C.; Wilson, J. R. H. Tetrahedron Lett. 2003, 44,
283–4286; (h) Yi, C. S.; Kwon, K.-H.; Lee, D. W. Org. Lett. 2009, 11, 1567–1569;
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Tong, X.; Xu, J. Org. Lett. 2005, 7, 263–266.
For selected examples on zinc catalyst, see: (a) Frantz, D. E.; Fassler, R.;
Carreira, E. M. J. Am. Chem. Soc. 1999, 121, 11245–11246; (b) Frantz, D. E.;
Fassler, R.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 1806–1807; (c) Boyall, D.;
Lopez, F.; Sasaki, H.; Frantz, D.; Carreira, E. M. Org. Lett. 2000, 2, 4233–4236; (d)
Anand, N. K.; Carreira, E. M. J. Am. Chem. Soc. 2001, 123, 9687–9688; (e) Fassler,
R.; Frantz, D. E.; Oetiker, J.; Carreira, E. M. Angew. Chem., Int. Ed. 2002, 41, 3054–
(polydimethylsiloxane with 5% phenyl groups, 30 m, 0.25 mm i.d., 0.25
film thickness) using helium carrier gas. General procedure for the oxidation of
diphenylmethane to benzophenone: In a 25 mL pressure tube, ZnBr (10 mol %)
and stirring bar were added. After the addition of diphenylmethane
(1 mmol), trifluoroacetic acid (0.2 mL) and 1,4-dioxane (2 mL) by syringe,
(4 mmol; 30% aqueous) was added in one pot to the solution and the final
lm
9
.
2
a
2 2
H O
solution was kept at 100 °C for 16 h. Then hexadecane (100 mg) and ethyl
acetate (3 mL) were injected, a part of solution was taken for GC and GC–MS
analysis after properly mixed. All the products are commercially available.
3
056; (f) Fischer, C.; Carreira, E. M. Org. Lett. 2004, 6, 1497–1499; (g) Topic, D.;
Aschwanden, P.; Fassler, R.; Carreira, E. M. Org. Lett. 2005, 7, 5329–5330; (h)