不饱和烃在碘催化下一锅法合成α-酮酰胺
收稿日期: 2015-02-08
修回日期: 2015-04-08
网络出版日期: 2015-04-10
基金资助
国家重点基础研究发展计划(No. 2015CB856500)资助项目.
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).
任相伟 , 王光伟 , 唐向阳 , 赵温涛 . 不饱和烃在碘催化下一锅法合成α-酮酰胺[J]. 有机化学, 2015 , 35(8) : 1733 -1738 . DOI: 10.6023/cjoc201502014
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
[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.
/
| 〈 |
|
〉 |