Article

One-Pot Domino Henry-Friedel-Crafts Alkylation Reaction in Deep Eutectic Solvent

  • Zhiyu Hu ,
  • Guofang Jiang ,
  • Zhiqiang Zhu ,
  • Bozhen Gong ,
  • Zongbo Xie ,
  • Zhanggao Le
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  • a Jiangxi Province Key Laboratory of Synthetic Chemistry, East China University of Technology, Nanchang, Jiangxi 330013

Received date: 2020-06-15

  Revised date: 2020-07-16

  Online published: 2020-08-27

Supported by

the National Natural Science Foundation of China(11765002); the Science and Technology Projects of Jiangxi Province(20192BBH80012)

Abstract

A green multicomponent reaction between aldehydes, nitromethane and N-substituted anilines in deep eutectic solvent (DES) has been developed. In this reaction, aldehydes and nitromethane underwent Henry reaction, followed by a Friedel-Crafts alkylation reaction with electron-rich arenes. The desired products were formed quickly in excellent yields under mild conditions without the need of any additional catalysts. The deep eutectic solvent (zinc chloride and choline chloride) is cheap and recyclable, which reduces the synthesis cost.

Cite this article

Zhiyu Hu , Guofang Jiang , Zhiqiang Zhu , Bozhen Gong , Zongbo Xie , Zhanggao Le . One-Pot Domino Henry-Friedel-Crafts Alkylation Reaction in Deep Eutectic Solvent[J]. Chinese Journal of Organic Chemistry, 2021 , 41(1) : 325 -332 . DOI: 10.6023/cjoc202006029

References

[1]
(a) Bandini M.; Melloni A.; Umani-Ronchi A. Angew. Chem., Int. Ed. 2004, 43, 550.
[1]
(b) Poulsen T.B.; Jørgensen K.A. Chem. Rev. 2008, 108, 2903.
[1]
(c) You S.-L.; Cai Q.; Zeng M. Chem. Soc. Rev. 2009, 38, 2190.
[1]
(d) Terrasson V.; Marcia de Figueiredo R.; Campagne J.M. Eur. J. Org. Chem. 2010, 2635.
[1]
(e) Rueping M.; Nachtsheim B.J. Beilstein J. Org. Chem. 2010, 6, 6.
[1]
(f) Naredla R.R.; Klumpp D.A. Chem. Rev. 2013, 113, 6905.
[2]
(a) Lancianesi S.; Palmieri A.; Petrini M. Chem. Rev. 2014, 114, 7108.
[2]
(b) Tang R.J.; Milcent T.; Crousse B. RSC Adv. 2018, 19, 10314.
[3]
Hayashi T.; Senda T.; Ogasawara T. J. Am. Chem. Soc. 2000, 122, 10716.
[4]
(a) Saxty G.; Woodhead S.J.; Berdini V.; Davies T.G.; Verdonk M.L.; Wyatt P.G.; Boyle R.G.; Barford D.; Downham R.; Garrett M.D.; Carr R.A. J. Med. Chem. 2007, 50, 2293.
[4]
(b) Burgey C.S.; Paone D.V.; Shaw A.W.; Deng J.Z.; Nguyen D.N.; Potteiger C.M.; Graham S.L.; Vacca J.P.; Williams T.M. Org. Lett. 2008, 10, 3235.
[5]
(a) Zhu J.P.; Bienaymé H. Multicomponent Reactions, John Wiley & Sons, Germany, 2006.
[5]
(b) Dömling A. Chem. Rev. 2006, 106, 17.
[6]
(a) Nicolaou K.C.; Chen J.S. Chem. Soc. Rev. 2009, 38, 2993.
[6]
(b) Touré B.B.; Hall D.G. Chem. Rev. 2009, 109, 4439.
[6]
(c) Yadav D.K.; Patel R.; Srivastava V.P.; Watal G.; Yadav L.D.S. Tetrahedron Lett. 2010, 51, 5701.
[7]
Oikawa Y.; Hirasawa H.; Yonemitsu O. Tetrahedron Lett. 1978, 19, 1759.
[8]
(a) Paras N.A.; MacMillan D.W.S. J. Am. Chem. Soc. 2002, 124, 7894.
[8]
(b) Guo Y.C.; Li D.P.; Li Y.L.; Wang H.M.; Xiao W.J. Chirality 2009, 21, 777.
[8]
(c) Zhou Y.; Li X.; Hou S.; Xu J. J. Mol. Catal. A :Chem. 2012, 365, 203.
[8]
(d) Yin W.; Ma Y.; Xu J.; Zhao Y. J. Org. Chem. 2006, 71, 4312.
[8]
(e) Wang X.; Wang Y.; Du D.M.; Xu J. J. Mol. Catal. A :Chem. 2006, 255, 31.
[8]
(f) Zhang Z.; Ma Y.; Zhao Y. Synlett 2008, 1091.
[8]
(g) Xu J.; Xia J.; Lan Y. Synth. Commun. 2005, 35, 2347.
[9]
Halimehjani A.Z.; Farvardin M.V.; Zanussi H.P.; Ranjbari M.A.; Fattahi M. J. Mol. Catal. A :Chem. 2014, 381, 21.
[10]
(a) Ruß C.; König B. Green Chem. 2012, 14, 2969.
[10]
(b) Zhang Q.; Vigier K.D.O.; Royer S.; Jerome F. Chem. Soc. Rev. 2012, 41, 7108.
[10]
(c) del Monte, F.; Carriazo, D.; Serrano, M.C.; Gutierrez, M.C.; Ferrer, M.L. ChemSusChem 2014, 7, 999.
[11]
Xie Z.B.; Li H.X.; Liu Y.S.; Lan J.; Hu Z.Y.; Le Z.G. Chin. J. Org. Chem. 2019, 39, 2632. (in Chinese)
[11]
( 谢宗波, 李红霞, 刘联胜, 兰金, 胡智宇, 乐长高, 有机化学, 2019, 39, 2632.).
[12]
(a) Abbott A.P.; Capper G.; Davies D.L.; Rasheed R.K. Tambyrajah V. Chem. Commun. 2003, 70.
[12]
(b) Abbott A.P.; Boothby D.; Capper G.; Davies D.L.; Rasheed R.K. J. Am. Chem. Soc. 2004, 126, 9142.
[12]
(c) Carriazo D.; Serrano M.C.; Gutierrez M.C.; Ferrer M.C.; del Monte, F.Chem. Soc. Rev. 2012, 41, 4996.
[13]
Santi V.D.; Cardellini F.; Brinchi L.; Germani R. Tetrahedron Lett. 2012, 53, 5151.
[14]
Azizi N.; Manocheri Z. Res. Chem. Intermed. 2012, 38, 1495.
[15]
Cristian V.; Francisco J.S.; Joaquín G.A. Catal. Commun. 2014, 44, 76.
[16]
Morales R.C.; Tambyrajah V.; Jenkins P.R.; Davies D.L.; Abbott A.P. Chem. Commun. 2004, 158.
[17]
Sonawane Y.A.; Phadtare S.B.; Borse B.N.; Jagtap A.R.; Shankarling G.S. Org. Lett. 2010, 12, 1456.
[18]
Friedel C.; Crafts J.M. J. Chem. Soc. 1877, 32, 725.
[19]
Chen G.Q.; Xie Z.B.; Ai F.; Chen Z.S.; Lan J.; Hu Z.Y.; Le Z.G. Heterocycles 2019, 98, 1189.
[20]
(a) Gao G.; Wang P.; Liu P.; Zhang W.; Zhang Z. Chin. J. Org. Chem. 2018, 38, 846. (in Chinese)
[20]
( 高歌, 王萍, 刘鹏, 张卫红, 默丽萍, 张占辉, 有机化学, 2018, 38, 846.).
[20]
(b) Chen G.Q.; Xie Z.B.; Liu Y.S.; Meng J.; Le Z.G. Chin. J. Org. Chem. 2020, 40, 156. (in Chinese)
[20]
( 陈国庆, 谢宗波, 刘一帅, 孟佳, 乐长高, 有机化学, 2020, 40, 156.).
[20]
(c) Xiong X.Q.; Han Q.; Si L.; Xiao S.Y.; Bi C. Chin. J. Org. Chem. 2016, 36, 480. (in Chinese)
[20]
( 熊兴泉, 韩骞, 石霖, 肖上运, 毕成, 有机化学, 2016, 36, 480.).
[20]
(d) Zhang M.; Liu T.H.; Shang Z.R.; Hu H.C.; Zhang Z.H. Catal. Commun. 2017, 88, 39.
[20]
(e) Liu P.; Hao J.W.; Mo L.P.; Zhang Z.H. RSC Adv. 2015, 5, 48675.
[20]
(f) Zhang M.; Liu P.; Shang Z.R.; Hu H.C.; Zhang Z.H. RSC Adv. 2016, 6, 106160.
[20]
(g) Zhang W.H.; Chen M.R.; Hao Y.; Jian X.; Zhou X.L.; Zhang Z.H. J. Mol. Liq. 2019, 278, 124.
[20]
(h) Ma C.T.; Liu P.; Wu W.; Zhang Z.H. J. Mol. Liq. 2017, 242, 606.
[21]
Singh B.S.; Lobo H.R.; Shankarling G.S. Catal. Commun. 2012, 24, 70.
[22]
(a) Zhang Y.Y.; Lu X.H.; Feng X.; Shi Y.J.; Ji X.Y. Prog. Chem. 2013, 25, 881. (in Chinese)
[22]
( 张盈盈, 路小华, 冯新, 史已俊, 吉晓燕, 化学进展, 2013, 25, 881.).
[22]
(b) Duan Z.; Gu Y.; Deng Y. Catal. Commun. 2006, 7, 651.
[22]
(c) Tao L.; Deng Y.F.; Gan S.C.; Chen J. Chin. J. Chem. Eng. 2010, 18, 322. (in Chinese)
[22]
( 龙涛, 邓岳锋, 甘树才, 陈继, 中国化学工程学报, 2010, 18, 322.).
[22]
(d) Inaloo I.D.; Majnooni S.; Esmaeilpour M. Eur. J. Org. Chem. 2018, 26, 3481.
[23]
Zarei M.; Noroozizadeh E.; Moosavi-Zare A.R.; Zolfigol M.A. J. Org. Chem. 2018, 83, 3645.
[24]
Mukhopadhyay C.; Tapasw P.K. Synth. Commun. 2012, 42, 2453.
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