Chinese Journal of Organic Chemistry >
FeCl3-Catalyzed Friedel-Crafts Alkylation of α-Hydroxy Ketene Dithioacetals with Indoles
Received date: 2015-02-06
Revised date: 2015-03-15
Online published: 2015-03-19
Supported by
Project supported by the National Natural Science Foundation of China (No. 20272008), the Science Technology Foundation of Anshan City (No. 2014KJ05) and the Science Technology Foundation of Anshan Normal University (No. 12kyxm05).
An inexpensive and environmentally friendly FeCl3 catalyzed Friedel-Crafts alkylation of α-hydroxy ketene dithioacetals with indoles including free-NH indoles and N or C(2)-substituted indoles has been developed. The reaction was efficiently performed in the presence of FeCl3 (2.5 mol%) at room temperature (25 ℃) in CH2Cl2, affording α-indolyl ketene dithioacetals in excellent yields. The procedure was characterized by lower amount of inexpensive catalyst, mild reaction condition, environmentally benign and similicity.
Zhao Hui , Zhang Fuwei , Yu Haifeng , Liao Peiqiu , Diao Quanping , Li Tiechun , Xin Guang , Hou Dongyan . FeCl3-Catalyzed Friedel-Crafts Alkylation of α-Hydroxy Ketene Dithioacetals with Indoles[J]. Chinese Journal of Organic Chemistry, 2015 , 35(7) : 1493 -1499 . DOI: 10.6023/cjoc201502008
[1] Stadler, D.; Bach, T. Angew. Chem., Int. Ed. 2008, 47, 7557.
[2] Womack, G. B.; Angeles, J. G.; Fanelli, V. E.; Indradas, B.; Snowden, R. L.; Sonnay, P. J. Org. Chem. 2009, 74, 5738.
[3] Cai, Y.; Zhu, S. F.; Wang, G. P.; Zhou, Q. L. Adv. Synth. Catal. 2011, 353, 2939.
[4] Padrón, J. I.; Martín, V. S. Top Organomet. Chem. 2011, 33, 1.
[5] Song, Y.; Tang, X. S.; Hou, X. M.; Bai, Y. J. Chin. J. Org. Chem. 2013, 33, 76 (in Chinese). (宋阳, 唐雪松, 侯晓萌, 白银娟, 有机化学, 2013, 33, 76.)
[6] Yang, Q.; Wang, L. D.; Guo, T. L.; Yu, Z. K. J. Org. Chem. 2012, 77, 8355.
[7] Wang, Y. M.; Bi, X. H.; Li, D. H.; Liao, P. Q.; Wang, Y. D.; Yang, J.; Zhang, Q.; Liu, Q. Chem. Commun. 2011, 47, 809.
[8] Huang, D. S.; Wang, H. N.; Xue, F. Z.; Shi, Y. A. J. Org. Chem. 2011, 76, 7269.
[9] Tang, L. N.; Pang, Y. L.; Yan, Q.; Shi, L. Q.; Huang, J. H.; Du, Y. F.; Zhao, K. J. Org. Chem. 2011, 76, 2744.
[10] Kochanowska-Karamyan, A. J.; Hamann, M. T. Chem. Rev. 2010, 110, 4489.
[11] Hibino, S.; Choshi, T. Nat. Prod. Rep. 2002, 19, 148.
[12] Bandini, M.; Eichholzer, A. Angew. Chem., Int. Ed. 2009, 48, 9608.
[13] Wang, C. C.; Xie, S. L.; Xie, Z. F. Chin. J. Org. Chem. 2013, 33, 1919 (in Chinese). (王春超, 谢绍雷, 解正峰, 有机化学, 2013, 33, 1919.)
[14] Lv, J.; Qin, Y.; Cheng, J. P.; Luo, S. Z. Acta Chim. Sinica 2014, 72, 809 (in Chinese). (吕健, 秦岩, 程津培, 罗三中, 化学学报, 2014, 72, 809.)
[15] Chen, S, J.; Lu, G. P.; Cai, C. Synthesis 2014, 46, 1717.
[16] Whitney, S.; Grigg, R.; Derrick, A.; Keep, A. Org. Lett. 2007, 9, 3299.
[17] Das, D.; Roy, S. Adv. Synth. Catal. 2013, 355, 1308.
[18] Putra, A. E.; Takigawa, K.; Tanaka, H.; Ito, Y.; Oe, Y.; Ohta, T. Eur. J. Org. Chem. 2013, 28, 6344.
[19] Zhang, L.; Zhu, Y. X.; Yin, G. W.; Lu, P.; Wang, Y. G. J. Org. Chem. 2012, 77, 9510.
[20] Sanz, R.; Martínez, A.; Miguel, D.; Álvarez-Gutiérrez, J. M.; Rodríguez, F. Adv. Synth. Catal. 2006, 348, 1841.
[21] Shirakawa, S.; Kobayashi, S. Org. Lett. 2007, 9, 311.
[22] Wang, M.; Sun, S. G.; Liang, D. Q.; Liu, B. Y.; Dong, Y.; Liu, Q. Eur. J. Org. Chem. 2011, 26, 2466.
[23] Guillena, G.; Ramón, D. J.; Yus, M. Angew. Chem., Int. Ed. 2007, 46, 2358.
[24] Jana, U.; Maiti, S.; Biswas, S. Tetrahedron Lett. 2007, 48, 7160.
[25] Pan, L.; Liu, Q. Synlett 2011, 1073.
[26] Pan, L.; Bi, X. H.; Liu, Q. Chem. Soc. Rev. 2013, 42, 1251.
[27] Liu, J.; Wang, M.; Li, B.; Liu, Q.; Zhao, Y. J. Org. Chem. 2007, 72, 4401.
[28] Piao, C. R.; Zhao, Y. L.; Han, X. D.; Liu, Q. J. Org. Chem. 2008, 73, 2264.
[29] Bi, X. H.; Dong, D. W.; Liu, Q. J Am Chem Soc. 2005, 127, 4578.
[30]
[30] Liang, D. Q.; Wang, M.; Bekturhun, B. Adv. Synth. Catal. 2010, 352, 1593.
[31] Yu, H. F.; Jin, W. W.; Sun, C. L.; Yu, Z. K. Angew. Chem., Int. Ed. 2010, 49, 5792.
[32] Yu, H. F.; Zhang, Y. M.; Li, T. C.; Liao, P. Q.; Diao, Q. P.; Xin, G.; Meng, Q. L.; Hou, D. Y. RSC Adv. 2015, 5, 11293.
[33] Jin, W. W.; Du, W. M.; Yang, Q.; Yu, H. F.; Yu, Z. K. Org Lett. 2011, 13, 4272.
[34] Dong, Y.; Wang, M.; Liu, J. Chem Commun. 2011, 47, 7380.
[35] Yu, H. F. Synth. Commun. 2013, 43, 1280.
[36] Yu, H. F.; Liao P. Q. Chemistry 2013, 76, 435 (in Chinese). (于海丰, 廖沛球, 化学通报, 2013, 76, 435.)
[37] Yu, H. F. Chin. J. Chem. 2012, 23, 367.
[38] Yu, H. F.; Liao P. Q. Chem. J. Chin. Univ. 2012, 33, 1969 (in Chinese). (于海丰, 廖沛球, 高等学校化学学报, 2012, 33, 1969.)
[39] Yu, H. F.; Wang, D. L.; Zhao, H.; Hou, D. Y. Chin. J. Org. Chem. 2011, 31, 949 (in Chiense). (于海丰, 王东来, 赵辉, 侯冬岩, 有机化学, 2011, 31, 949.)
[40] Yu, H. F.; Yu, Z. K. Angew. Chem., Int. Ed. 2009, 48, 2929.
[41] Yu, H. F.; Li, T. C.; Liao, P. Q. Synthesis 2012, 44, 3743.
[42] Yu, H. F.; Li, T. C.; Liao, P. Q.; Diao, Q. P.; Xin, G.; Hou, D. Y. Chin. J. Org. Chem. 2014, 34, 956 (in Chinese). (于海丰, 李铁纯, 廖沛球, 刁全平, 辛广, 侯冬岩, 有机化学, 2014, 34, 956.)
[43] Yu, H. F.; Liao P. Q.; Diao, Q. P.; Li, T. C.; Xin, G.; Han, L. N.; Hou, D. Y. Chin. J. Org. Chem. 2014, 34, 1851 (in Chinese). (于海丰, 廖沛球, 刁全平, 李铁纯, 辛广, 韩立楠, 侯冬岩, 有机化学, 2014, 34, 1851.)
/
| 〈 |
|
〉 |
