4-OH-TEMPO/TCQ/TBN/HCl: A Metal-Free Catalytic System for Aerobic Oxidation of Alcohols under Mild Conditions
Yanli Dong
School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China
Search for more papers by this authorXiaomei Zhao
School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China
Search for more papers by this authorCorresponding Author
Renhua Liu
School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China
School of Pharmacy, East China University of Science and Technology, Shanghai 200237, ChinaSearch for more papers by this authorYanli Dong
School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China
Search for more papers by this authorXiaomei Zhao
School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China
Search for more papers by this authorCorresponding Author
Renhua Liu
School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China
School of Pharmacy, East China University of Science and Technology, Shanghai 200237, ChinaSearch for more papers by this authorAbstract
A green and economical catalyst system, 4-OH-TEMPO/TCQ/TBN/HCl, for the aerobic oxidation of a broad range of primary and secondary alcohols to the corresponding carbonyl compounds has been developed. These reactions proceed without transition-metals under mild conditions with excellent yields.
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REFERENCES
- 1 Hudlicky, M., Oxidations in Organic Chemistry, American Chemical Society, Washington, DC, 1990.
- 2a Kotha, S. S.; Chandrasekar, S.; Sahu, S.; Sekar, G.. Eur. J. Org. Chem., 2014, 2014, 7451.
- 2b Jiang, J.-A.; Du, J.-L.; Wang, Z.-G.; Zhang, Z.-N.; Xu, X.; Zheng, G.-L.; Ji, Y.-F.. Tetrahedron Lett., 2014, 55, 1677.
- 2c Steves, J. E.; Stahl, S. S.. J. Am. Chem. Soc., 2013, 135, 15742.
- 2d Rahimi, A.; Azarpira, A.; Kim, H.; Ralph, J.; Stahl, S. S.. J. Am. Chem. Soc., 2013, 135, 6415.
- 2e Hoover, J. M.; Ryland, B. L.; Stahl, S. S.. J. Am. Chem. Soc., 2013, 135, 2357.
- 2f Shibuya, M.; Osada, Y.; Sasano, Y.; Tomizawa, M.; Iwabuchi, Y.. J. Am. Chem. Soc., 2011, 133, 6497.
- 2g Kantam, M. L.; Pal, U.; Sreedhar, B.; Bhargava, S.; Iwasawa, Y.; Tada, M.; Choudary, B. M.. Adv. Synth. Catal., 2008, 350, 1225.
- 3a Ryland, B. L.; Stahl, S. S.. Angew. Chem., Int. Ed., 2014, 53, 8824.
- 3b Zhang, H.; Fu, L.. Synth. Commun., 2014, 44, 610.
- 3c Shi, X.-J.; Qian, J.; Tan, F.-F.; Yu, C.-M.. J. Chem. Res., 2013, 37, 398.
- 3d Shi, Y.; Nabae, Y.; Hayakawa, T.; Kakimoto, M.-a.. RSC Adv., 2015, 5, 1923.
- 3e Mase, N.; Mizumori, T.; Tatemoto, Y.. Chem. Commun., 2011, 47, 2086.
- 3f Yin, W.; Chu, C.; Lu, Q.; Tao, J.; Liang, X.; Liu, R.. Adv. Synth. Catal., 2010, 352, 113.
- 3g Attoui, M.; Vatele, J.-M.. Synlett, 2014, 25, 2923.
- 3h Shen, J.; Sun, J.; Qin, S.. Chin. J. Chem., 2014, 32, 405.
- 3i Karimi, B.; Rafiee, M.; Alizadeh, S.; Vali, H.. Green Chem., 2015, 17, 991.
- 3j Beejapur, H. A.; Campisciano, V.; Franchi, P.; Lucarini, M.; Giacalone, F.; Gruttadauria, M.. ChemCatChem, 2014, 6, 2419.
- 3k Aellig, C.; Scholz, D.; Conrad, S.; Hermans, I.. Green Chem., 2013, 15, 1975.
- 3l Liu, D.; Zhou, H.; Gu, X.; Shen, X.; Li, P.. Chin. J. Chem., 2014, 32, 117.
- 4 Liu, R.; Liang, X.; Dong, C.; Hu, X.. J. Am. Chem. Soc., 2004, 126, 4112.
- 5 Xie, Y.; Mo, W.; Xu, D.; Shen, Z.; Sun, N.; Hu, B.; Hu, X.. J. Org. Chem., 2007, 72, 4288.
- 6 Wang, X.; Liu, R.; Jin, Y.; Liang, X.. Chem. Eur. J., 2008, 14, 2679.
- 7 Liu, Q.; Lu, M.; Yang, F.; Wei, W.; Sun, F.; Yang, Z.; Huang, S.. Syn. Commun., 2010, 40, 1106.
- 8 Yang, G.; Wang, W.; Zhu, W.; An, C.; Gao, X.; Song, M.. Synlett, 2010, 3, 437.
- 9 Tao, J.; Lu, Q.; Chu, C.; Liu, R.; Liang, X.. Synthesis, 2010, 23, 3974.
- 10 Rahimi, A.; Azarpira, A.; Kim, H.; Ralph, J.; Stahl, S. S.. J. Am. Chem. Soc., 2013, 135, 6415.
- 11 Zhang, J.; Jiang, Z.; Zhao, D.; He, G.; Zhou, S.; Han, S.. Chin. J. Chem., 2013, 31, 794.
- 12 Shibuya, M.; Osada, Y.; Sasano, Y.; Tomizawa, M.; Iwabuchi, Y.. J. Am. Chem. Soc., 2011, 133, 6497.
- 13a Shibuya, M.; Tomizawa, M.; Suzuki, I.; Iwabuchi, Y.. J. Am. Chem. Soc., 2006, 128, 8412.
- 13b Shibuya, M.; Doi, R. S.; Shibuta, T.; Uesugi, S.-i.; Iwabuchi, Y.. Org. Lett., 2012, 14, 5006.
- 13c Hayashi, M.; Sasano, Y.; Nagasawa, S.; Shibuya, M.; Iwabuchi, Y.. Chem. Pharm. Bull., 2011, 59, 1570.
- 13d Shibuya, M.; Tomizawa, M.; Sasano, Y.; Iwabuchi, Y.. J. Org. Chem., 2009, 74, 4619.
- 13e Tomizawa, M.; Shibuya, M.; Iwabuchi, Y.. Org. Lett., 2009, 11, 1829.
- 14 Qiu, C.; Jin, L.; Huang, Z.; Tang, Z.; Lei, A.; Shen, Z.; Sun, N.; Mo, W.; Hu, B.; Hu, X.. ChemCatChem, 2012, 4, 76.