Chinese Journal of Organic Chemistry >
Iodine-Catalyzed One-Pot Synthesis of α-Ketoamides from Unsaturated Hydrocarbons
Received date: 2015-02-08
Revised date: 2015-04-08
Online published: 2015-04-10
Supported by
Project supported by the National Basic Research Program of China (No. 2015CB856500).
A one-pot synthetic protocol of α-ketoamides from alkene or alkyne using iodine as catalyst and tert-butyl hydroperoxide as oxidant is reported. The protocol has the advantages of good atomic economy, mild reaction condition, high yielding, and avoiding using heavy metal catalyst, which has solved the drawbacks of harsh condition, poor availability of starting materials, and low yielding in previous α-ketoamides systhesis. α-Ketoamides has potential applications in bioactive molecule and drug synthesis.
Key words： α-ketoamide; alkenes; alkynes; iodine; tert-butyl hydroperoxide
Ren Xiangwei , Wang Guangwei , Tang Xiangyang , Zhao Wentao . Iodine-Catalyzed One-Pot Synthesis of α-Ketoamides from Unsaturated Hydrocarbons[J]. Chinese Journal of Organic Chemistry, 2015 , 35(8) : 1733 -1738 . DOI: 10.6023/cjoc201502014
[1] (a) Fusetani, N.; Matsunaga, S.; Matsumoto, H.; Takebayashi, Y. J. Am. Chem. Soc. 1990, 112, 7053. (b) Crowley, C. A.; Delaet, N. G. J.; Ernst, J.; Grove, C. G.; Hepburn, B.; King, B.; Larson, C. J.; Miller, S.; Pryor, K.; Shuster, L. J. WO 2007146712, 2007 [Chem. Abstr. 2007, 148, 70192]. (c) Sheha, M. M.; Mahfouz, N. M.; Hassan, H. Y.; Youssef, A. F.; Mimoto T.; Kiso, Y. Eur. J. Med. Chem. 2000, 35, 887. (d) Patel D. V.; Gless R. D. J.; Webb H.; Heather K.; Anandan S. K.; Aavula B. R. WO 2008073623, 2008 [Chem. Abstr. 2008, 149, 79227].
[2] (a) Dubowchik, G. M.; Ditta, J. L; Herbst, J. J.; Bollini, S.; Vinitsky, A. Bioorg. Med. Chem. Lett. 2000, 10, 559. (b) Singh, R. P.; Shreeve, J. M. J. Org. Chem. 2003, 68, 6063. (c) Sai, K. K. S.; Esteves, P. M.; da Penha, E. T.; Klumpp, D. J. Org. Chem. 2008, 73, 6506. (d) Tomita, D.; Yamatsugu, K.; Kanai, M.; Shibasak, M. J. Am. Chem. Soc. 2009, 131, 6946.
[3] (e) Yang, L.; Wang, D.-X.; Huang, Z.-T.; Wang, M.-X. J. Am. Chem. Soc. 2009, 131, 10390.
[4] (a) Zhang, C.; Jiao, N. J. Am. Chem. Soc. 2009, 132, 28. (b) Zhang, C.; Xu, Z.; Zhang, L.; Jiao, N. Angew. Chem., Int. Ed. 2011, 50, 11088.
[5] (a) Shao, Y.; Wu, Z.; Miao, C.; Liu, L. J. Organomet. Chem. 2014, 767, 60. (b) Wang, H.; Guo, L. N.; Duan, X.-H. Org. Biomol. Chem. 2013, 11, 4573. (c) Zhang, X.; Yang, W.; Wang, L. Org. Biomol. Chem. 2013, 11, 3649. (e) Mupparapu, N.; Khan, S.; Battula, S.; Kushwaha, M.; Gupta, A. P.; Ahmed, Q. N.; Vishwakarma, R. A. Org. Lett. 2014, 16, 1152.
[6] (a) Genelot, M.; Villandier, N.; BendJeriou, A.; Jaithong, P.; DJakovitch, L.; Dufaud, V. Catal. Sci. Technol. 2012, 2, 1886. (b) Liu, J.; Zhang, R.; Wang, S.; Sun, W.; Xia, C. Org. Lett. 2009, 11, 1321. (c) Papp, M.; Skoda-Foldes, R. J. Mol. Catal. A: Chem. 2013, 378, 193. (d) Tsukada, N.; Ohba, Y.; Inoue, Y. J. Organomet. Chem. 2003, 687, 436.
[7] (a) Lamani, M.; Prabhu, K. R. Chem. Eur. J. 2012, 18, 14638. (b) Zhang, Z.; Su, J.; Zha, Z.; Wang, Z. Chem. Commun. 2013, 49, 8982. (c) Wei, W.; Shao, Y.; Hu, H.; Zhang, F.; Zhang, C.; Xu, Y.; Wan, X. Org. Lett. 2012, 77, 7157.
[8] Zhang, X.; Wang, L. Green Chem. 2012, 14, 2141.
[9] Zhang, C.; Zong, X.; Zhang, L.; Jiao, N. Org. Lett. 2012, 14, 3280.
[10] He, T.; Li, H.; Li, P.; Wang, L. Chem. Commun. 2011, 47, 8946.
[11] He, T.; Yu, L.; Zhang, L.; Wang, L.; Wang, M. Org. Lett. 2011, 13, 5016.
[12] (a) Kalmode, H. P.; Vadagaonkar, K. S.; Chaskar, A. C. RSC Adv. 2014, 4, 60316. (b) Deshidi, R.; Devari, S.; Shah, B. A. Eur. J. Org. Chem. 2015, 1428. (c) Vadagaonkar, K. S.; Kalmode, H. P.; Murugan, K.; Chaskar, A. C. RSC Adv. 2015, 5, 5580.
[13] Evans, R. D.; Schauble, J. H. Synthesis 1986, 727.
[14] (a) Kornblum, N.; Powers, J. W.; Anderson, G. J.; Jones, W. J.; Larson, H. O.; Levand, O.; Weaver, W. M. J. Am. Chem. Soc. 1957, 79, 6562. (b) Jiang, H.; Huang, H.; Cao, H.; Qi, C. Org. Lett. 2010, 12, 5561.
[15] (a) Deshidi, R.; Kumar, M.; Devari, S.; Shah, B. A. Chem. Comm. 2014, 50, 9533. (b) The possibility that oxygen, TBHP, or iodine might participate the oxidation could not be ruled out in current stage: Mupparapu, N.; Battini, N.; Battula, S.; Khan, S.; Vishwakarma, R. A.; Ahmed, Q. N. Chem. Eur. J. 2015, 21, 2954. (c) TBHP oxidation: Zhang, X.; Wang, M.; Zhang, Y.; Wang, L. RSC Adv. 2013, 3, 1311. (d) TBHP/I2 oxidation: Wei, W.; Shao, Y.; Hu, H.; Zhang, C.; Xu, Y.; Wan, X. J. Org. Chem. 2012, 77, 7157.
[16] Konstantinova, L. S.; Bol'shakov, O. I.; Obruchnikova, N. V.; Golova, S. P.; Nelyubina, Y. V.; Lyssenko, K. A.; Rakitin, O. A. Tetrahedron 2010, 66, 4330.
/
| 〈 |
|
〉 |
