AEROBIC OXIDATION OF BENZYLIC HALIDES
1113
1
1
1
1
1. Moorthy, J. N.; Singhal, N.; Senapati, K. Oxidations with IBX: Benzyl halides to
carbonyl compounds, and the one-pot conversion of olefins to 1,2-diketones. Tetrahedron
Lett. 2006, 47, 1757.
2. Goswami, S.; Jana, S.; Dey, S.; Adak, A. K. A simple and convenient manganese dioxide
oxidation of benzyl halides to aromatic aldehydes under neutral condition. Chem. Lett.
2005, 34, 194.
3. Cardillo, G.; Orena, M.; Sandri, S. Chromate ion as a synthetically useful nucleophile: A
novel synthesis of aldehydes from alkyl halides. J. Chem. Soc., Chem. Commun. 1976, 6,
190.
4. Brown, R. E.; Hansen, H. V.; Lustgarten, D. M.; Stanaback, R. J.; Meltzer, R. I.; Aza
steroids, V: Introduction of 11-hydroxy and 11-amino groups. J. Org. Chem. 1968, 33,
4180.
1
1
5. McKillop, A.; Ford, M. E. An improved procedure for the conversion of benzyl halides
into benzaldehydes. Synth. Commun. 1974, 4, 45.
6. Khodaei, M. M.; Khosropour, A. R.; Mahbubeh, J. Bi(NO ) ꢃ 5H O ꢃ TBAF as an
3
3
2
efficient reagent for in situ oxidation: Dihydropyrimidinone formation from benzyl
halides. Synthesis 2005, 1301.
1
7. Liu, Q.; Lu, M.; Sun, F.; Li, J.; Zhao, Y. Oxidation of benzyl halides to aldehydes and
ketones with potassium nitrate catalyzed by phase transfer catalyst in aqueous media.
Synth. Commun. 2008, 38, 4188.
1
8. Yadav, G. D.; Mistry, C. K. A new model of capsule membrane phase transfer catalysis
for oxidation of benzyl chloride to benzaldehyde with hydrogen peroxide. J. Mol. Catal.
A: Chem. 1995, 102, 67.
1
9. Kumar, R.; Bhaumik, A. Triphase, solvent-free catalysis over the TS-1=H O system in
2
2
selective oxidation reactions. Micropor. Mesopor. Mater. 1998, 21, 497.
0. Tang, J. T.; Zhu, J. L.; Shen, Z. X.; Zhang, Y. W. Efficient and convenient oxidation of
organic halides to carbonyl compounds by H in ethanol. Tetrahedron Lett. 2007, 48,
919.
2
2 2
O
1
2
1. Li, C.; Zheng, P.; Li, J.; Zheng, H.; Cui, Y.; Shao, Q.; Ji, X.; Zhang, J.; Zhao, P.; Xu, Y.
The dual roles of oxodiperoxovanadate both as a nucleophile and an oxidant in the green
oxidation of benzyl alcohols or benzyl halides to aldehydes and ketones. Angew. Chem.
Int. Ed. 2003, 42, 5063.
2
2
2. Goswami, S.; Mahapatra, A. K. Aromatic aldehydes from benzylbromides via
cobalt(I)-mediated benzyl radicals in the presence of aerial oxygen: A mild oxidation reac-
tion in neutral condition. Tetrahedron Lett. 1998, 39, 1981.
3. Hashemi, M. M.; Beni, Y. A. Copper (I) chloride=kieselguhr: A versatile catalyst for oxi-
dation of alkyl halides and alkyl tosylates to the carbonyl compounds. J. Chem. Res.
Synop. 1999, 434.
24. Itoh, A.; Kodama, T.; Inagaki, S.; Masaki, Y. Photooxidation of arylmethyl bromides
with mesoporous silica FSM-16. Org. Lett. 2000, 2, 2455.
25. Liu, Q.; Lu, M.; Li, Y.; Li, J. Effect of organic electrolyte on chloromethylation of
2-bromoethylbenzene in micellar catalytic system. J. Mol. Catal. A: Chem. 2007,
277, 113.
2
6. Liu, R. H.; Liang, X. M.; Dong, C. Y.; Hu, X. Q. Transition-metal-free: A highly efficient
catalytic aerobic alcohol oxidation process. J. Am. Chem. Soc. 2004, 126, 4112.
7. Herrerias, C. I.; Zhang, T. Y.; Li, C. J. Catalytic oxidation of alcohols to carbonyl com-
pounds by oxygen under solvent-free and transition-metal-free conditions. Tetrahedron
Lett. 2006, 47, 13.
2
2
28. Wang, X. L.; Liu, R. H.; Jin, Y.; Liang, X. M. TEMPO=HCl=NaNO catalyst: A
transition-metal-free approach to efficient aerobic oxidation of alcohols to aldehydes
and ketones. Chem. Eur. J. 2008, 14, 2679.