S. Rani, B. R. Bhat / Tetrahedron Letters 51 (2010) 6403–6405
6405
Table 2 (continued)
Alcohols
Product
Yield of carbonyl compoundb (%)
FeL1
FeL2
FeL3
FeL4
O
OH
H
79.7
77.2
76.3
77.8
NO2
NO2
OH
O
75.6
71.9
73.8
70.8
74.8
71.4
75.2
69.8
H
OH
O
OH
O
70.5
36.8
68.9
33.6
69.4
35.2
70.1
36.1
CH3
H3C
O
OH
H3C
H3C
H3C
H3C
H
OH
O
28.3
23.1
26.5
20.6
25.0
22.6
27.6
22.9
H
O
H3C
H3C
OH
OH
H3C
H3C
CH3
CH3
H
H
22.3
20.5
21.6
22.1
O
a
1 mmol alcohol, 5.0 mmol H2O2, 0.04 mmol Fe(III) complex, 10 mL CH3CN, stirring at 80 °C.
GC yield, average of three trials.
b
5. (a) Nakamura, Y.; Egami, H.; Matsumoto, K.; Uchida, T.; Katsuki, T. Tetrahedron
2007, 63, 6383; (b) Egami, H.; Shimizu, H.; Katsuki, T. Tetrahedron Lett. 2005, 46,
783.
6. (a) Vishal Sharma, B.; Suman Jain, L.; Sain, B. J. Mol. Catal. A: Chem. 2004, 212,
55; (b) Das, S.; Punniyamurthy, T. Tetrahedron Lett. 2003, 44, 6033.
7. (a) Velusamy, S.; Srinivasan, A.; Punniyamurthy, T. Tetrahedron Lett. 2006, 47,
923; (b) Istva Marko, E.; Paul Giles, R.; Tsukazaki, M.; Stephen Brown, M.; Urch,
C. J. Science 1996, 274, 2044.
In conclusion, oxidation of alcohols using hydrogen peroxide, a
mild oxidant, in the presence of catalytic amounts of synthesized
iron(III) complexes provides a simple, safe, and efficient method
for oxidation of aromatic alcohols to corresponding carbonyls with
high yield.
8. (a) Shul’pina, L. S.; Veghini, D.; Kudinov, A. R.; Shulpin, G. B. React. Kinet. Catal.
Lett. 2006, 88, 157; (b) Alette Ligtenbarg, G. J.; Oosting, P.; Roelfes, G.; Crois, R.
La. M.; Lutz, M.; Anthony Spek, L.; Hage, R.; Feringa, B. L. Chem. Commun. 2001,
385; (c) Klopstra, M.; Hage, R.; Kellogg, R. M.; Feringa, B. L. Tetrahedron Lett.
2003, 44, 4581; (d) Shil, X.-y.; Wei, J.-F. J. Mol. Catal. A: Chem. 2005, 229, 13; (e)
Balogh Hergovicha, E.; Speier, G. J. Mol. Catal. A: Chem. 2005, 230, 79.
10. Procedure: A solution of the complexes (0.04 mmol) in 10 ml acetonitrile
was added to the solution of substrate (1 mmol) and H2O2 (5 mmol, 30%).
The reaction mixture was stirred at 80 °C for 90 min. The residue was then
extracted with a minimal volume of ether and dried over MgSO4. The ether
solution was then analyzed by GC using dichlorobenzene as internal
standard.
References and notes
1. (a) Trost, B. M.; Fleming, I. In Comprehensive Organic Synthesis; Pergamon Press:
UK, 1991. p 7; (b) Corey, E. J.; Barrette, E.-P.; Plato Magriotis, A. Tetrahedron Lett.
1985, 26, 5855; (c) Firouzabadi, H.; Iranpoor, N.; Kueiezadeh, F.; Toofan, J.
Tetrahedron Lett. 1986, 42, 719.
2. (a) Pawel, J. F.; Jaroslaw Sobczak, M.; Jozef Ziolkowski, J. Chem. Commun. 2004,
244; (b) Lingaiah, N.; Mohan Reddy, K.; Seshu Babu, N.; Narasimha Rao, K.;
Suryanarayana, I.; Sai Prasad, P. S. Catal. Commun. 2006, 7, 245.
3. (a) Mitchell Schultz, J.; Candice Park, C.; Matthew Sigman, S. Chem. Commun.
2002, 3034; (b) Karimi, B.; Zamani, A. J. Iran. Chem. Soc. 2008, 5, S1–S20.
4. (a) Ankush Biradar, V.; Mohan Dongare, K.; Shubhangi Umbarkar, B.
Tetrahedron Lett. 2009, 50, 2885; (b) Gharah, N.; Chakraborty, S.; Alok
Mukherjee, K.; Bhattacharyya, R. Inorg. Chim. Acta 2009, 362, 1089.