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Selective Aerobic Oxidation of Benzylic Alcohols Catalyzed by CuBr/1,8-Diazabicyclo[5.4.0]undec-7-ene
Received date: 2018-06-28
Revised date: 2018-09-03
Online published: 2018-09-05
A novel and practical cuprous bromide-catalyzed aerobic oxidation of benzylic alcohols with 1,8-diazabicyclo-[5.4.0]undec-7-ene (DBU) as the additive under air atmosphere has been developed. Various primary and secondary benzylic alcohols and allylic alcohols were smoothly transformed into the corresponding aldehydes and ketones with high yields and selectivity. The process is 2,2,6,6-tetramethylpiperidin-1-oxyl (TEMPO) free and solvent-free.
Cai Liangzhen , Huang Zhen , Yang Liqun , Xie Xiaomin , Tao Xiaochun . Selective Aerobic Oxidation of Benzylic Alcohols Catalyzed by CuBr/1,8-Diazabicyclo[5.4.0]undec-7-ene[J]. Chinese Journal of Organic Chemistry, 2018 , 38(12) : 3326 -3331 . DOI: 10.6023/cjoc201806044
[1] Tojo, G; Fernández, M. Oxidation of Alcohols to Aldehydes and Ketones. Basic Reactions in Organic Synthesis, Springer, New York, 2006.
(b) Mallat, T.; Baiker, A. Chem. Rev. 2004, 104, 3037.
(c) Awad, O. I.; Mamat, R.; Ali, O. M.; Sidik, N. A. C.; Yusaf, T.; Kadirgama, K.; Kettner, M. Renewable Sustainable Energy Rev. 2018, 82, 2586.
(d) Allen, Scott E.; Walvoord, R. R.; Padilla-Salinas, R.; Ko-zlowski, M. C. Chem. Rev. 2013, 113, 6234.
[2] Constable, D. J. C.; Dunn, P. J.; Hayler, J. D.; Humphrey, G. R.; Leazer, J. L.; Linderman, R.; Lorenz, K.; Manley, J.; Pearlman, B. A.; Wells, A.; Zaks, A.; Zhang, T. Green Chem. 2007, 9, 411.
[3] (a) Sigman, M. S.; Jensen, D. R. Acc. Chem. Res. 2006, 39, 221.
(b) Zhang, G.; Wang, Y.; Wen, X.; Ding, C.; Li, Y. Chem. Commun. 2012, 2979.
(c) Gligorich, K. M.; Sigman, M. S. Chem. Commun. 2009, 3854.
(d) Gao, M.; Chen, M.; Li, Y.; Tang, H.; Ding, H.; Wang, K.; Yang, L.; Li, C.; Lei, A. Asian J. Org. Chem. 2017, 6, 1566.
[4] (a) Guan, B.; Xing, D.; Cai, G.; Wan, X.; Yu, N.; Fang, Z.; Yang, L.; Shi, Z. J. Am. Chem. Soc. 2005, 127, 18004.
(b) Miyamura, H.; Matsubara, R.; Miyazaki, Y.; Kobayashi, S. Angew. Chem., Int. Ed. 2007, 46, 4151.
[5] (a) Mizuno, N.; Yamaguchi, K. Catal. Today 2008, 132, 18.
(b) Hasan, M.; Musawir, M.; Kozhevnikov, I. J. Mol. Catal. A 2002, 180, 77.
[6] (a) Crabtree, R. H. Chem. Rev. 2017, 117, 9228.
(b) Parmeggiani, C.; Cardona, F. Green Chem. 2012, 14, 547.
(c) Schultz, M. J.; Sigman, M. S. Tetrahedron 2006, 62, 8227.
[7] (a) Evano, G.; Blanchard, N.; Toumi, M. Chem. Rev. 2008, 108, 3054.
(b) Ryland, B. L.; Stahl, S. S. Angew. Chem., Int. Ed. 2014, 53, 8824.
(c) Wendlandt, A. E.; Suess, A. M.; Stahl, S. S. Angew. Chem., Int. Ed. 2011, 50, 11062.
(d) Faisca Phillips, A. M.; Pombeiro, A. J. L.; Kopylovich, M. N. ChemCatChem 2017, 9, 217.
[8] (a) Das, O.; Paine, T. K. Dalton Trans. 2012, 41, 11476.
(b) Munakata, M.; Nishibayashi, S.; Sakamoto, H. J. Chem. Soc., Chem. Commun. 1980, 219.
(c) Liu, X.; Qiu, A.; Sawyer, D. T. J. Am. Chem. Soc. 1993, 115, 3239.
(d) Skibida, I.; Sakharov, A. Catal. Today 1996, 27, 187.
(e) Korpi, H.; Figiel, P. J.; Lankinen, E.; Ryan, P.; Leskelä, M.; Repo, T. Eur. J. Inorg. Chem. 2007, 2465.
[9] (a) Jallabert, C.; Riviere, H. Tetrahedron Lett. 1977, 14, 1215.
(b) Jallabert, C.; Riviere, H. Tetrahedron 1980, 36, 1191.
[10] (a) Semmelhack, M. F.; Schmid, C. R.; Cortes, D. A.; Chou, C. S. J. Am. Chem. Soc. 1984, 106, 3374.
(b) Hoover, J. M.; Stahl, S. S. J. Am. Chem. Soc. 2011, 133, 16901.
(c) Hoover, J. M.; Ryland, B. L.; Stahl, S. S. J. Am. Chem. Soc. 2013, 135, 2357.
(d) Wang, L.; Bie, Z.; Shang, S.; Lv, Y.; Li, G.; Niu, J. Y.; Gao, S. RSC Adv. 2016, 6, 35008.
(e) Marais, L.; Burés, J.; Jordaan, J. H. L.; Mapolie, S.; Swarts, A. J. Org. Biomol. Chem. 2017, 15, 6926.
(f) Zhang, G.; Han, X.; Luan, Y.; Wang, Y.; Wen, X.; Ding, C. Chem. Commun. 2013, 49, 7908.
(g) Betzemeier, B.; Cavazzini, M.; Quici, S.; Knochel, P. Tetrahedron Lett. 2000, 41, 4343.
(h) Sun, N.; Zhang, X.; Jin, L.; Hu, B.; Shen, Z.; Hu, X. Catal. Commun. 2017, 101, 5.
[11] (a) Markó, I.; Gautier, A.; Giles, P. R.; Tsukazaki, M.; Brown, S. M. Science 1996, 20, 2044.
(b) Markó, I.; Gautier, I.; Dumeunier, R.; Doda, K.; Philippart, F.; Brown, S. M.; Urch, C. J. Angew. Chem., Int. Ed. 2004, 43, 1588.
[12] (a) Chaudhuri, P.; Hess, M.; Mueller, J.; Hildenbrand, K.; Bill, E.; Weyhermueller, T.; Wieghardt, K. J. Am. Chem. Soc. 1999, 121, 9599.
(b) Itoh, S.; Taki, M.; Takayama, S.; Nagatomo, S.; Kitagawa, T.; Sakurada, N.; Arakawa, R.; Fukuzumi, S. Angew. Chem., Int. Ed. 1999, 38, 2774.
(c) Wang, Y.; DuBois, J. L.; Hedman, B.; Hodgson, K. O.; Stack, T. D. P. Science 1998, 279, 537.
(d) Thomas, F.; Gellon, G.; Gautier-Luneau, I.; Saint-Aman, E.; Pierre, J. L. Angew. Chem., Int. Ed. 2002, 41, 3047.
[13] Xu, B.; Lumb, J. P.; Arndtsen; B. A. Angew. Chem., Int. Ed. 2015, 54, 4208.
[14] Konev, M. O.; Jarvo. E. R. ACS Cent. Sci. 2017, 3, 272.
[15] Liang, L.; Rao, G.; Sun, H.-L.; Zhang, J.-L. Adv. Synth. Catal. 2010, 352, 2371.
[16] Xu, Q.; Xie, H.; Chen, P,; Yu, L.; Chen, J.; Hu, X. Green Chem. 2015, 17, 2774.
[17] Lahtinen, P.; Lankinen, E.; Leskelä, M.; Repo, T. Appl. Catal., A 2005, 295, 177.
[18] (a) Zhang, L.; Zhang, Y.; Wang, X.; Shen, J. Molecules 2013, 18, 654.
(b) Thakur, K. G.; Sekar, G. Synthesis. 2009, 2785.
(c) Wei, W.-T.; Zhou, M.-B.; Fan, J.-H.; Liu, W.; Song, R.-J.; Liu, Y.; Hu, M.; Xie, P.; Li, J.-H. Angew. Chem., Int. Ed. 2013, 52, 3638.
(d) Williams, B. N.; Benitez, D.; Miller, K. L.; Tkatchouk, E.; Goddard, W. A.; Diaconescu P. L. J. Am. Chem. Soc. 2011, 133, 4680.
[19] Porcheddu, A.; Giacomelli, G.; Piredda, I. J. Comb. Chem. 2009, 11, 126.
[20] Zhang, Z.; Huang, B.; Qiao, G.; Zhu, L.; Xiao, F.; Chen. F.:Fu, B.; Zhang, Z. Angew. Chem., Int. Ed. 2017, 56, 4320.
[21] Miao, C.-X.; He, L.-N.; Wang, J.-L.; Wu, F. J. Org. Chem. 2010, 75, 257.
[22] Jiang, N.; Ragauskas, A. J. Org. Lett. 2005, 7, 3689.
[23] Lee, K.; Maleczka, R. E. Org. Lett. 2006, 8, 1887.
[24] Furuya, T.; Strom, A. E.; Ritter, T. J. Am. Chem. Soc. 2009, 131, 1662.
[25] Kashparova, V. P.; Klushin, V. A.; Kashparova, V. P.; Klushin, V. A.; Zhukova, I. Y.; Kashparov, I. S.; Chernysheva, D. V.; Il'chibaeva, I. B.; Smirnova, N. V.; Kagan, E. Sh.; Chernyshev, V. M. Tetrahedron Lett. 2017, 58, 3517.
[26] Chittimalla, S. K.; Chang, T.-C.; Liu, T.-C.; Hsieh, H.-P.; Liao, C.-C. Tetrahedron 2008, 64, 2586.
[27] Li, X.; Zhao, J.; Zhang, L.; Hu, M.; Wang, L.; Hu, J. Org. Lett. 2015, 17, 298.
[28] Kim, B.-R.; Lee, H.-G.; Kim, E.-J.; Lee, S.-G.; Yoon, Y.-J. J. Org. Chem. 2010, 75, 484.
[29] Layek, K.; Maheswaran, H.; Arundhathi, R.; Kantam, M. L.; Bhargava, S. K. Adv. Synth. Catal. 2011, 353, 606.
[30] Mamane, V.; Aubert, E.; Fort, Y. J. Org. Chem. 2007, 72, 7294.
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