FeCl3-Catalyzed Friedel-Crafts Alkylation of α-Hydroxy Ketene Dithioacetals with Indoles

doi:10.6023/cjoc201502008

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (7): 1493-1499.DOI: 10.6023/cjoc201502008 Previous Articles Next Articles

Articles

FeCl₃催化的α-羟基二硫缩烯酮与吲哚的Friedel-Crafts烷基化反应

赵辉^a, 张福维^a, 于海丰^a, 廖沛球^b, 刁全平^a, 李铁纯^a, 辛广^a, 侯冬岩^a

a 鞍山师范学院化学与生命科学学院鞍山 114007;
b 东北师范大学化学学院长春 130024

收稿日期:2015-02-06 修回日期:2015-03-15 发布日期:2015-03-19
通讯作者: 于海丰 E-mail:yuhf68105@sina.com
基金资助:
国家自然科学基金(No. 20272008)、鞍山市科技基金(No. 2014KJ05)和鞍山师范学院科技基金(No. 12kyxm05)资助项目.

FeCl₃-Catalyzed Friedel-Crafts Alkylation of α-Hydroxy Ketene Dithioacetals with Indoles

Zhao Hui^a, Zhang Fuwei^a, Yu Haifeng^a, Liao Peiqiu^b, Diao Quanping^a, Li Tiechun^a, Xin Guang^a, Hou Dongyan^a

a School of Chemistry and Life Science, Anshan Normal University, Anshan 114007;
b Department of Chemistry, Northeast Normal University, Changchun 130024

Received:2015-02-06 Revised:2015-03-15 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).

1. FeCl₃-Catalyzed Friedel-Crafts Alkylation of α-Hydroxy Ketene Dithioacetals with Indoles.PDF(3600KB)

Abstract

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.

Key words: iron (III) chloride, ketene dithioacetals, alcohols, indole derivatives, Friedel-Crafts alkylation

Cite this article

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]. Chin. J. Org. Chem., 2015, 35(7): 1493-1499.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[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.)

FeCl₃催化的α-羟基二硫缩烯酮与吲哚的Friedel-Crafts烷基化反应

FeCl₃-Catalyzed Friedel-Crafts Alkylation of α-Hydroxy Ketene Dithioacetals with Indoles

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Boyu Yan, Jieliang Wu, Jinfei Deng, Dan Chen, Xiushen Ye, Qiuli Yao. Recent Progress in Light-Driven Direct Dehydroxylation and Derivation of Alcohols [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3055-3066.
[2]	Xiaoyu Zhang, Xinyan Li, Bing Cui, Zhihui Shao, Mingqin Zhao. Design, Synthesis and Antioxidant Activity of Tetrahydro-β-carbolines [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2885-2894.
[3]	Yanhua Gao, Yinpan Zhang, Yan Zhang, Tao Song, Yong Yang. Visible-Light-Induced Aerobic Oxidation of Alcohols over Surface Oxygen Vacancies-Enriched Nb₂O₅ [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2572-2579.
[4]	Jiantao Zhang, Yawen Deng, Nuolin Mo, Lianfen Chen. Advances in Radical Mediated 1,2-Aryl Migration Reactions of α,α-Diarylallyl Alcohols [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 426-435.
[5]	Wei Wang, Zheyu Zhang, Xue Zhang, Haifeng Yu, Hui Luo, Dongyue Huo, Yupeng Xu, Xiaobo Zhao. Synthesis of Polysubstituted 2,3-Dihydropyridin-4(1H)-one in Water [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 742-750.
[6]	Meijiao Sun, Jing Tan, Yu Tan, Jinsong Peng, Chunxia Chen. Pd-Catalyzed C(2)—H Arylation of 3-(2-Aminopyrimidin-4-yl)indoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3945-3959.
[7]	Tiantian Liu, Xinhong Duan. Recent Progress in the Construction of Chiral 3-Substituted Indoles by Asymmetric Friedel-Crafts Reactions [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3695-3712.
[8]	Tianyu Chen, Feng Han, Shuangyan Li, Jianping Liu, Jianhui Chen, Qing Xu. Transition Metal-Free Selective Aerobic C-Alkylation of Methyl N-Heteroarenes with Alcohols [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2914-2924.
[9]	Zexin Huang, Yuqiang Yin, Fengcheng Jia, Anxin Wu. Research Progress on C2—C3 Bond Cleavage of Indole and Its Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2028-2044.
[10]	Qingyun Gu, Zhenfeng Cheng, Xiaobao Zeng. Electrochemical Oxidative Trifluoromethylation of α-Oxoketene Ketene Dithioacetals with CF₃SO₂Na [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1537-1544.
[11]	Yunrong Chen, Wei Liu, Xiaoyu Yang. Recent Advances in Kinetic Resolution of Tertiary Alcohols [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 679-697.
[12]	Jiahao Liu, Shidong Zhang, Zihong Luan, Yan Liu, Zhuofeng Ke. Ruthenium Catalyzed Selective Acceptorless Dehydrogenation of Allylic Alcohols to α,β-Unsaturated Carbonyls [J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4361-4369.
[13]	Jianing Che, Tao Song, Xianchi Gao, Yong Yang. Borrowing Hydrogen Reductive Coupling of Nitroarenes with Benzyl Alcohols to Imines Catalyzed by Pd Nanoparticles on N Doped Carbon Materials [J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 276-283.
[14]	Ma Xiantao, Yu Jing, Wang Zilong, Zhang Yun, Zhou Qiuju. Efficient Activation of Allylic Alcohols in Pd-Catalyzed Allylic Substitution Reactions [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2669-2677.
[15]	Zhang Shunji, Liu Huili. Sulfuric Acid Catalyzed Rapid Nucleophilic Substitution of Propargyl Alcohols [J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1257-1265.

FeCl3催化的α-羟基二硫缩烯酮与吲哚的Friedel-Crafts烷基化反应