芳香化合物的电化学C—H键官能化研究进展
|
摘要
C—H键是有机化合物中最基本和最广泛的化学键.利用电化学方法实现芳香化合物C—H键的官能化和直接转化可以避免反应物的预官能化,是一种绿色可持续且更具有原子经济性的转化途径.该方法借助阳极上的氧化反应实现芳香化合物C—H键的官能化,完成C—X键(X=C、N、O、S)的构建和稠环化合物的合成,无需使用氧化剂.通过控制电极材料、电解质和溶剂等条件,也可以实现特定的化学选择性和区域选择性.综述了近年来芳香化合物的电化学C—H键官能化这一领域的研究进展.
Carbon-hydrogen bonds are the most extensive and basic chemical bonds existed in organic compounds. Electrochemical functionalization and direct conversion of aromatic C—H bonds is a green, sustainable, and atomically economical transformation pathway, which avoids the pre-functionalization of reactants. The anodic electrooxidation of aromatics allows the formation of C—X(X=C, N, O, S) bonds and the preparation of fused aromatic rings without the use of oxidants. Certain C—H activation reactions with chemoselectivity and regioselectivity can also be achieved by the optimization of electrode materials, electrolytes, and solvents. Vourious reactions focusing on the electrochemical functionalizations of C—H bonds in aromatic compounds are mainly reviewed.
Carbon-hydrogen bonds are the most extensive and basic chemical bonds existed in organic compounds. Electrochemical functionalization and direct conversion of aromatic C—H bonds is a green, sustainable, and atomically economical transformation pathway, which avoids the pre-functionalization of reactants. The anodic electrooxidation of aromatics allows the formation of C—X(X=C, N, O, S) bonds and the preparation of fused aromatic rings without the use of oxidants. Certain C—H activation reactions with chemoselectivity and regioselectivity can also be achieved by the optimization of electrode materials, electrolytes, and solvents. Vourious reactions focusing on the electrochemical functionalizations of C—H bonds in aromatic compounds are mainly reviewed.
引文
[1]Yan, M.; Kawamata, Y.; Baran, P. S. Chem. Rev. 2017, 117, 13230.
[2]Horn, E. J.; Rosen, B. R.; Baran, P. S. ACS Cent. Sci. 2016, 2, 302.
[3]Jiang, Y.; Xu, K.; Zeng, C. Chem. Rev. 2018, 118, 4485.
[4]Li, Z.; Li, C. J.; Herrerías, C. I.; Yao, X. Chem. Rev. 2007, 107, 6.
[5]Bergman, R. G. Nature 2007, 466, 391.
[6]Sun, C. L.; Li, B. J.; Shi, Z. J. Chem. Rev. 2011, 111, 1293.
[7]Liao,K.;Pickel,T.C.;Boyarskikh,V.;Bacsa,J.;Musaev,D.G.;Davies, H. Nature 2016, 47, 230.
[8]Evan, J. H.; Brandon, R. R.; Yong, C.; Tang, J. Z.; Ke, C.; Eastgate,M. D.; Baran, P. S. Nature 2016, 533, 77.
[9]Liu,W.; Zheng, X. Y.; Zeng, J.G.;Cheng, P. Chin.J. Org. Chem.2017, 37, 1(in Chinese).(刘薇,郑昕宇,曾建国,程辟,有机化学, 2017, 37, 1.)
[10]Liu, Y. R.; Hu, B. L.; Zhang, X. G. Chin. J. Chem. 2017, 35, 307
[11]Pei,P.K.;Zhang,F.;Yi,H.;Lei,A.W.ActaChimi.Sinica2017,75, 15(in Chinese).(裴朋昆,张凡,易红,雷爱文,化学学报, 2017, 75, 15.)
[12]Li,T.T.;Jin,P.Y.;Lin,S.;Zhi,Y.G.;Liu,X.Y.Chin.J.Chem.2016, 34, 490.
[13]Schopohl,M.C.;Faust,A.;Mirk,D.;Fr?hlich,R.;Kataeva,O.Eur. J. Org. Chem. 2010, 2987.
[14]Waldvogel, S. R.; Mirk, D. Tetrahedron Lett. 2000, 31, 4769.
[15]Malkowsky, I. M.; Griesbach, U.; Pütter, H.; Waldvogel, S. R. Eur.J. Org. Chem. 2006, 4569.
[16]Kirste,A.;Martin, N.;Malkowsky, I. M.; Florian, S.;Andreas, F.;Waldvogel, S. R. Chem. Eur. J. 2009, 15, 2273
[17]Kirste, A.; Gregor, S.; Waldvogel, S. R. Org. Lett. 2011, 13, 3126.
[18]Kirste,A.;Shotaro,H.;Gregor,S.;Malkowsky,I.M.;Florian,S.;Andreas,F.;Toshio,F.;Waldvogel,S.R.Chem.-Eur.J.2011,17,14164.
[19]Kirste,A.;Gregor,S.;Florian,S.;Andreas,F.;Waldvogel,S.R.Angew. Chem., Int. Ed. 2010, 49, 971.
[20]Kirste,A.;Elsler,B.;Schnakenburg,G.;Waldvogel,S.R.J.Am.Chem. Soc. 2012, 43, 3571.
[21]Bernd,E.;Anton,W.;Dieter,S.;Dyballa,K.M.;Franke,R.;Waldvogel, S. R. Chem.-Eur. J. 2015, 21, 12321.
[22]Sebastian,L.;Anton,W.;Bernd,E.;Dieter,S.;Dyballa,K.M.;Franke,R.;Waldvogel,S.R.Angew.Chem.,Int.Ed.2016,55,10872.
[23]Bernd,E.;Dieter,S.;Marie,D.K.;Franke,R.;Waldvogel,S.R.Angew. Chem., Int. Ed. 2014, 53, 5210.
[24]Anton, W.; Dieter, S.; Dyballa, K. M.; Franke, R.; Waldvogel, S. R.Angew. Chem., Int. Ed. 2016, 55, 11180.
[25]Amatore,C.;Cammoun,C.;Jutand,A.Adv.Synth.Catal.2007,349, 292.
[26]Saito,F.;Aiso,H.;Kochi,T.;Kakiuchi,F.Organometallics2014,33, 6704.
[27]Ma, C.; Zhao, C. Q.; Li, Y. Q.; Zhang, L. P.; Xu, X. T.; Zhang, K.;Mei, T. S. Chem. Commun. 2017, 53, 12189.
[28]Jensen,K.L.;Franke,P.T.;Nielsen,L.T.;Daasbjerg,K.;Joergensen, K. A. Angew. Chem., Int. Ed. 2010, 122, 133.
[29]Ho,X.H.;Mho,S.I.;Kang,H.;Jang,H.Y.Eur.J.Org.Chem.2010, 4436.
[30]Fu, N.; Li, L.; Yang, Q.; Luo, S. Z. Org. Lett. 2017, 19, 2122.
[31]Li, L. J.; Jiang, Y. Y.; Lam, C. M.; Zeng, C. C.; Hu, L. M.; Little, R.D. J. Org. Chem. 2015, 80, 11021.
[32]Lara, S.; Enders, M.; Bernd, E.; Dieter, S.; Dyballa, K. M.; Franke,R.; Waldvogel, S. R. Angew. Chem. Int. Ed. 2017, 56, 4877.
[33]R?se, P.; Emge, S.; K?nig, C. A.; Hilt, G. Adv. Synth. Catal. 2017,359, 1359.
[34]Morofuji, T.; Shimizu, A.; Yoshida, J. Angew. Chem., Int. Ed. 2012,51, 7259.
[35]Arai, T.; Hiroyuki, T.; Nakabayashi, K.; Kashiwagi, T.; Mahito, A.Chem. Commun. 2015, 51, 4891.
[36]Gallardo, I.; Gonzalo, G.. Eur. J. Org. Chem. 2008, 2463.
[37]Moutiers,G.;Pinson,J.;Terrier,F.;Goumont,R.Chem.-Eur.J.2001, 7, 1712.
[38]Charushin,V.N.;Chupakhin,O.N.InTopicsinHeterocyxlic Chemistry, Ed.:Selig, P., Springer International Publishing, Cham.2013, Vol. 37, pp. 1~50.
[39]Gallardo, I.; Guirado, G.; Marquet, J. Chem.-Eur. J. 2001, 7, 1759.
[40]Gallardo, I.; Gonzalo, G.; Marquet, J. J. Org. Chem. 2002, 67, 2548.
[41]Gallardo, I.; Gonzalo, G.; Marquet, J. J. Org. Chem. 2003, 68, 631.
[42]Gallardo, I.; Gonzalo, G.; Marquet, J. J. Org. Chem. 2003, 68, 7334.
[43]Gallardo, I.; Guirado, G.; Marquet, J. Eur. J. Org. Chem. 2002, 261.
[44]Wang, Q. Q.; Xu, K.; Jiang, Y. Y.; Liu, Y. G.; Sun, B. G.; Zeng, C.C. Org. Lett. 2017, 19, 5517.
[45]Morofuji, T.; Shimizu, A.; Yoshida, J. J. Am. Chem. Soc. 2013, 135,5000.
[46]M?hle,S.;Herold,S.;Richter,F.;Nefzger,H.;Waldvogel,S.R.ChemElectroChem 2017, 4, 2196.
[47]Herold,S.;M?hle,S.;Zirbes,M.;Richter,F.;Nefzger,H.;Waldvogel, S. R. Eur. J. Org. Chem. 2016, 1274.
[48]Morofuji, T.; Shimizu, A.; Yoshida, J. J. Am. Chem. Soc. 2014, 136,4496.
[49]Morofuji, T.; Shimizu, A.; Yoshida, J. J. Am. Chem. Soc. 2015, 137,9816.
[50]Watts, K.; Gattrell, W.; Beilstein, T. J. Org. Chem, 2011, 7, 1108.
[51]Nishiyama, S.; Amano, Y. Tetrahedron Lett. 2006, 37, 6505.
[52]Broese, T.; Francke, R. Org. Lett. 2016, 18, 5896.
[53]Gao, W. J.; Li, W. C.; Zeng, C. C.; Tian, H. Y.; Hu, L. M.; Little, R. D. J. Org. Chem. 2014, 79, 9613.
[54]Liang, S.; Zeng, C. C.; Tian, H. Y.; Sun, B. G.; Luo X. G.; Ren F. Z.J. Org. Chem. 2016, 2016, 11157.
[55]Gao, X. L.; Wang, P.; Zeng, L.; Tang, S.; Lei, A. W. J. Am. Chem.Soc. 2018, 140, 4195
[56]Gallardo,I.;Guirado,G.;Marquet,J.Eur.J.Org.Chem.2002,2002, 251.
[57]Hussey, C. L.; Achord, J. M. Annal. Dogmatic Theology 1981, 128,2556.
[58]Cortona,M.N.;Vettorazzi,N.R.;Silber,J.J.;Sereno,L.E.J.Electroanal. Chem. 1999, 470, 157.
[59]Nematollahi, D.; Ariapad, A.; Rafiee, M. J. Electrochem. Soc. 2007,602, 37.
[60]Salahifar, E.; Nematollahi, D.; Bayat, M.; Mahyari, A.; Rudbari, H.A. Org. Lett. 2015, 17, 4666.
[61]Tajima, T.; Kishi, Y.; Atsushi, N. Electrochim. Acta 2009, 54, 5959.
[62]Dudkina, Y. B.; Mikhaylov, D. Y.; Gryaznova, T. V.; Tufatullin, A.I.; Kataeva, O. N.; David, A. V.; Budnikova, Y. H. Organometallics2013, 32, 4785.
[63]Dudkina, Y. B.; Gryaznova, T. V.; Sinyashin, O. G.; Budnikova, Y.H. Russ. Chem. Bull. 2015, 64, 1713.
[64]Li, Yi. Q.; Yang, Q. L.; Fang, P.; Mei, T. S.; Zhang, D. Y. Org. Lett.2017, 19, 2905.
[65]Shrestha, A.; Lee, M.; Dunn, A. L.; Sanford, M. S. Org. Lett. 2018,20, 204.
[66]Sauermann,N.;Meyer,T.H.;Tian,C.;Ackermann,L.J.Am.Chem. Soc. 2017, 139, 18452.
[67]Nishiyama, S.; Yamamura, S. Synlett 2002, 533.
[68]Kazuki,M.;Takahashi,M.;Yamamura,S.;Nishiyama,S.Tetrahedron 2001, 57. 5527.
[69]Kawabata,Y.;Naito,Y.;Saitoh,T.;Kawa,K.;Fuchigami,T.;Nishiyama, S. Eur. J. Org. Chem. 2013, 99.
[70]Naito,Y.;Tanabe,T.;Yuki,K.;Ishikawa,Y.;Nishiyama,S.Tetrahedron Lett. 2010, 51, 4776.
[71]Tanabe,T.;Doi,F.;Ogamino,T.;Nishiyama,S.TetrahedronLett.2004, 45, 3477.
[72]Barjau, J.; Schnakenburg, G.; Waldvogel, S. R. Angew. Chem., Int.Ed. 2011, 50, 1415.
[73]Michael, M.; Lars, A.; Caroline, S.; Joaquin, B.; Dieter, S.; Till, O.;Arne, L.; Siegfried, R. W. Eur. J. Org. Chem. 2015, 4876.
[74]Barjau,J.;Schnakenburg,G.;Waldvogel,S.R.Synthesis2011,2054.
[75]Barjau, J.; K?nigs, P.; Kataeva, O.; Waldvogel, S. R.Synlett 2008,2309.
[76]Nematollahi, D.; Tammari, E. J. Org. Chem. 2005, 70, 7769.
[77]Zeng,C.C.;Liu,F.J.;Ping.D.W.;Cai,Y.L.;Zhong,R.G.;Becker, J. Y. J. Electroanal. Chem. 2009, 625, 131.
[78]Zeng, C. C.; Liu, F. J.; Ping, D. W.; Hu, L. M.; Cai, Y. L.; Zhong, R.G.. Tetrahedron 2009, 65, 4505.
[79]Zeng, C. C.; Ping, D. W.; Zhang, S. C.; Zhong, R. G.; Becker, J. Y.J. Electroanal. Chem. 2008, 622, 90.
[80]Khodaei,M.M.;Alizadeh,A.;Pakravan,N.J.Org.Chem.2008,73, 2527.
[81]Fotouhi, L.; Asadi, S.; Tammari, E.; Heravi, M. M.; Nematollahi, D.Anal. Bioanal. Electrochem. 2009, 1, 216.
[82]Amani, A.; Nematollahi, D. J. Org. Chem. 2012, 77, 11130.
[83]Wang, P.; Tang, S.; Huang, P. F.; Lei, A. W. Angew. Chem., Int. Ed.2017, 56, 3009.
[84]Nematollahi, D. N.; Ramazanali, R.; Maryam, M. Synth. Commun.2003, 34, 2269.
[85]Nematollahi,D.;Beiginejad,H.;Varmaghani,F.;Bayat,M.;Salehzadeh, H. J. Electrochem. Soc. 2013, 160, 142.
[86]Zeng,C.C.;Liu,C.F.;Zeng,J.;Zhong,R.G..J.Electroanal.Chem. 2007, 608, 85.
[87]Xiao,H.L.;Yang,C.W.;Zhang,N.T.;Zeng,C.C.;Hu,L.M.;Tian, H. Y.; Little, R. D. Tetrahedron 2013, 69, 658.
[88]Feng, M.L.; Xi,L. Y.; Chen,S. Y.; Yu, X.Q. Eur. J. Org. Chem.2017, 2017, 2746.
[89]Hou, Z. W.; Mao, Z. Y.; Zhao, H. B.; Melcamu, Y. Y.; Lu, X.; Song,J.; Xu, H. C. Angew. Chem., Int. Ed. 2016, 55, 9168.
[90]Hou,Z.W.;Mao,Z.Y.;Song,J.;Xu,H.C.ACSCatal.2017,7,5810.
[91]Wu, Z. J.; Xu, H. C. Angew. Chem., Int. Ed. 2017, 56, 4631.
[92]Xiong, P.; Xu, H.; Song, J. S.; Xu, H. C. J. Am. Chem. Soc. 2018,140, 2460.
[93]Tang, S.; Gao, X. L.; Lei, A. W. Chem. Commun. 2017, 53, 3354.
[94]Wen, J. W.; Shi, W. Y.; Zhang, F.; Liu, D.; Tang, S.; Wang, H. M.;Lin, X. M.; Lei, A. W. Org. Lett. 2017, 19, 3131.
[95]Zhao, H. B.; Hou, Z. W.; Liu, Z. J.; Zhou, Z. F.; Song, J. S.; Xu, H.C. Angew. Chem. Int. Ed. 2017, 56, 587.
[96]Zhao, H. B.; Liu, Z. J.; Song, J.; Xu, H. C. Angew. Chem., Int. Ed.2017, 56, 12732.
[97]Inoue, K.; Ishikawa, Y.; Nishiyama, S. Org. Lett. 2010, 12. 436.
[98]Kajiyama,D.;Inoue,K.;Ishikawa,Y.;Nishiyama,S.Tetrahedron2010, 66, 9779.
[99]Amano, Y.; Inoue, K.; Nishiyama, S. Synlett. 2008, 134.
[100]Morofuji,T.;Shimizu,A.;Yoshida,J.Chem.-Eur.J.2015,21,3211.
[101]Wesenberg, L. J.;Herold, S.; Shimizu, A.; Yoshida, J.; Waldvogel,S. R. Chem.-Eur. J. 2017, 23, 12096.
[102]Xu,F.;Qian,X.Yang.;Li,Y.J.;Xu,H.C.Org.Lett.2017,19,6332.
[103]Tile,G.;Anton,K.;Dieter,S.;Moeller,K.D.;Waldvogel,S.R.Chem. Commun. 2017, 53, 2974.
[104]Tile, G.; Anton, K.; Dieter, S.; Moeller, K. D.; Waldvogel, S. R. J.Am. Chem. Soc. 2017, 139, 12317
[105]Zhang, S.; Li, L. J.; Wang, H. Q.; Li, Q.; Liu, W. M.; Xu. K, Zeng,C. C. Org. Lett. 2018, 20, 252.
[106]Qian,X.Y.;Li,S.Q.;Song,J.S.;Xu,H.C.ACSCatal.2017,7,2730.
[107]Wang, P.; Tang, S.; Lei, A. W. Green Chem. 2017, 19, 2092.
[108]Folgueiras-Amador,A.A.;Qian,X.Y.;Xu,H.C.;Wirth,T.Chem.-Eur. J. 2018, 24, 487.
[109]Chiba, K.; Fukuda, M.; Kim, S.; Kitano, Y.; Tada, M. J. Org. Chem.2000, 31, 7654.
[110]Elseedi, H. R.; Yamamura, S.; Nishiyama, S. Tetrahedron 2002, 58,7485.
[111]Kim,S.;Noda,S.;Hayashi,K.;Chiba,K.Org.Lett.2008,10,1827.
[112]Kim, S.; Hirose, K.; Uematsu, J.; Mikami, Y.; Chiba, K. Chem.-Eur.J. 2012, 18, 6284.
[113]Liu, K.; Tang, S.; Huang, P. F.; Lei, A. W. Nat. Commun. 2017, 8,775.
[114]Tian, C.; Massignan, L.;Meyer, Tjark. H.;Ackermann, L. Angew.Chem., Int. Ed. 2018, 57, 2383.
[115]Xu, F.; Li, Y. Jie.; Huang, C.; Xu, H. C. ACS Catal. 2018, 8, 3820..
[116]Nematollahi,D.;Habibi,D.;Rahmati,M.;Rafiee,M.J.Org.Chem. 2004, 69, 2637.
[117]Hosseiny Davarani, S. S.; Nematollahi, D.; Shamsipur, M.; Najafi,N. M.; Masoumi, L.; Ramyar, S. J. Org. Chem. 2006, 71, 2139.
[118]Salehzadeh, H.; Nematollah, D.; Hesari, H. Green Chem. 2014, 45,2441.
[119]Zeng, C. C.; Liu, F. J.; Ping, D. W.; Hu, L. M.; Cai, Y. L.; Zhong, R.G.. J. Org. Chem. 2010, 41, 6386.
[120]Bai, Y. X.; Ping, D. W.; Little, R. D.; Tian, H. Y.; Hu, L. M.; Zeng,C. C. Tetrahedron 2011, 67, 9334.
[2]Horn, E. J.; Rosen, B. R.; Baran, P. S. ACS Cent. Sci. 2016, 2, 302.
[3]Jiang, Y.; Xu, K.; Zeng, C. Chem. Rev. 2018, 118, 4485.
[4]Li, Z.; Li, C. J.; Herrerías, C. I.; Yao, X. Chem. Rev. 2007, 107, 6.
[5]Bergman, R. G. Nature 2007, 466, 391.
[6]Sun, C. L.; Li, B. J.; Shi, Z. J. Chem. Rev. 2011, 111, 1293.
[7]Liao,K.;Pickel,T.C.;Boyarskikh,V.;Bacsa,J.;Musaev,D.G.;Davies, H. Nature 2016, 47, 230.
[8]Evan, J. H.; Brandon, R. R.; Yong, C.; Tang, J. Z.; Ke, C.; Eastgate,M. D.; Baran, P. S. Nature 2016, 533, 77.
[9]Liu,W.; Zheng, X. Y.; Zeng, J.G.;Cheng, P. Chin.J. Org. Chem.2017, 37, 1(in Chinese).(刘薇,郑昕宇,曾建国,程辟,有机化学, 2017, 37, 1.)
[10]Liu, Y. R.; Hu, B. L.; Zhang, X. G. Chin. J. Chem. 2017, 35, 307
[11]Pei,P.K.;Zhang,F.;Yi,H.;Lei,A.W.ActaChimi.Sinica2017,75, 15(in Chinese).(裴朋昆,张凡,易红,雷爱文,化学学报, 2017, 75, 15.)
[12]Li,T.T.;Jin,P.Y.;Lin,S.;Zhi,Y.G.;Liu,X.Y.Chin.J.Chem.2016, 34, 490.
[13]Schopohl,M.C.;Faust,A.;Mirk,D.;Fr?hlich,R.;Kataeva,O.Eur. J. Org. Chem. 2010, 2987.
[14]Waldvogel, S. R.; Mirk, D. Tetrahedron Lett. 2000, 31, 4769.
[15]Malkowsky, I. M.; Griesbach, U.; Pütter, H.; Waldvogel, S. R. Eur.J. Org. Chem. 2006, 4569.
[16]Kirste,A.;Martin, N.;Malkowsky, I. M.; Florian, S.;Andreas, F.;Waldvogel, S. R. Chem. Eur. J. 2009, 15, 2273
[17]Kirste, A.; Gregor, S.; Waldvogel, S. R. Org. Lett. 2011, 13, 3126.
[18]Kirste,A.;Shotaro,H.;Gregor,S.;Malkowsky,I.M.;Florian,S.;Andreas,F.;Toshio,F.;Waldvogel,S.R.Chem.-Eur.J.2011,17,14164.
[19]Kirste,A.;Gregor,S.;Florian,S.;Andreas,F.;Waldvogel,S.R.Angew. Chem., Int. Ed. 2010, 49, 971.
[20]Kirste,A.;Elsler,B.;Schnakenburg,G.;Waldvogel,S.R.J.Am.Chem. Soc. 2012, 43, 3571.
[21]Bernd,E.;Anton,W.;Dieter,S.;Dyballa,K.M.;Franke,R.;Waldvogel, S. R. Chem.-Eur. J. 2015, 21, 12321.
[22]Sebastian,L.;Anton,W.;Bernd,E.;Dieter,S.;Dyballa,K.M.;Franke,R.;Waldvogel,S.R.Angew.Chem.,Int.Ed.2016,55,10872.
[23]Bernd,E.;Dieter,S.;Marie,D.K.;Franke,R.;Waldvogel,S.R.Angew. Chem., Int. Ed. 2014, 53, 5210.
[24]Anton, W.; Dieter, S.; Dyballa, K. M.; Franke, R.; Waldvogel, S. R.Angew. Chem., Int. Ed. 2016, 55, 11180.
[25]Amatore,C.;Cammoun,C.;Jutand,A.Adv.Synth.Catal.2007,349, 292.
[26]Saito,F.;Aiso,H.;Kochi,T.;Kakiuchi,F.Organometallics2014,33, 6704.
[27]Ma, C.; Zhao, C. Q.; Li, Y. Q.; Zhang, L. P.; Xu, X. T.; Zhang, K.;Mei, T. S. Chem. Commun. 2017, 53, 12189.
[28]Jensen,K.L.;Franke,P.T.;Nielsen,L.T.;Daasbjerg,K.;Joergensen, K. A. Angew. Chem., Int. Ed. 2010, 122, 133.
[29]Ho,X.H.;Mho,S.I.;Kang,H.;Jang,H.Y.Eur.J.Org.Chem.2010, 4436.
[30]Fu, N.; Li, L.; Yang, Q.; Luo, S. Z. Org. Lett. 2017, 19, 2122.
[31]Li, L. J.; Jiang, Y. Y.; Lam, C. M.; Zeng, C. C.; Hu, L. M.; Little, R.D. J. Org. Chem. 2015, 80, 11021.
[32]Lara, S.; Enders, M.; Bernd, E.; Dieter, S.; Dyballa, K. M.; Franke,R.; Waldvogel, S. R. Angew. Chem. Int. Ed. 2017, 56, 4877.
[33]R?se, P.; Emge, S.; K?nig, C. A.; Hilt, G. Adv. Synth. Catal. 2017,359, 1359.
[34]Morofuji, T.; Shimizu, A.; Yoshida, J. Angew. Chem., Int. Ed. 2012,51, 7259.
[35]Arai, T.; Hiroyuki, T.; Nakabayashi, K.; Kashiwagi, T.; Mahito, A.Chem. Commun. 2015, 51, 4891.
[36]Gallardo, I.; Gonzalo, G.. Eur. J. Org. Chem. 2008, 2463.
[37]Moutiers,G.;Pinson,J.;Terrier,F.;Goumont,R.Chem.-Eur.J.2001, 7, 1712.
[38]Charushin,V.N.;Chupakhin,O.N.InTopicsinHeterocyxlic Chemistry, Ed.:Selig, P., Springer International Publishing, Cham.2013, Vol. 37, pp. 1~50.
[39]Gallardo, I.; Guirado, G.; Marquet, J. Chem.-Eur. J. 2001, 7, 1759.
[40]Gallardo, I.; Gonzalo, G.; Marquet, J. J. Org. Chem. 2002, 67, 2548.
[41]Gallardo, I.; Gonzalo, G.; Marquet, J. J. Org. Chem. 2003, 68, 631.
[42]Gallardo, I.; Gonzalo, G.; Marquet, J. J. Org. Chem. 2003, 68, 7334.
[43]Gallardo, I.; Guirado, G.; Marquet, J. Eur. J. Org. Chem. 2002, 261.
[44]Wang, Q. Q.; Xu, K.; Jiang, Y. Y.; Liu, Y. G.; Sun, B. G.; Zeng, C.C. Org. Lett. 2017, 19, 5517.
[45]Morofuji, T.; Shimizu, A.; Yoshida, J. J. Am. Chem. Soc. 2013, 135,5000.
[46]M?hle,S.;Herold,S.;Richter,F.;Nefzger,H.;Waldvogel,S.R.ChemElectroChem 2017, 4, 2196.
[47]Herold,S.;M?hle,S.;Zirbes,M.;Richter,F.;Nefzger,H.;Waldvogel, S. R. Eur. J. Org. Chem. 2016, 1274.
[48]Morofuji, T.; Shimizu, A.; Yoshida, J. J. Am. Chem. Soc. 2014, 136,4496.
[49]Morofuji, T.; Shimizu, A.; Yoshida, J. J. Am. Chem. Soc. 2015, 137,9816.
[50]Watts, K.; Gattrell, W.; Beilstein, T. J. Org. Chem, 2011, 7, 1108.
[51]Nishiyama, S.; Amano, Y. Tetrahedron Lett. 2006, 37, 6505.
[52]Broese, T.; Francke, R. Org. Lett. 2016, 18, 5896.
[53]Gao, W. J.; Li, W. C.; Zeng, C. C.; Tian, H. Y.; Hu, L. M.; Little, R. D. J. Org. Chem. 2014, 79, 9613.
[54]Liang, S.; Zeng, C. C.; Tian, H. Y.; Sun, B. G.; Luo X. G.; Ren F. Z.J. Org. Chem. 2016, 2016, 11157.
[55]Gao, X. L.; Wang, P.; Zeng, L.; Tang, S.; Lei, A. W. J. Am. Chem.Soc. 2018, 140, 4195
[56]Gallardo,I.;Guirado,G.;Marquet,J.Eur.J.Org.Chem.2002,2002, 251.
[57]Hussey, C. L.; Achord, J. M. Annal. Dogmatic Theology 1981, 128,2556.
[58]Cortona,M.N.;Vettorazzi,N.R.;Silber,J.J.;Sereno,L.E.J.Electroanal. Chem. 1999, 470, 157.
[59]Nematollahi, D.; Ariapad, A.; Rafiee, M. J. Electrochem. Soc. 2007,602, 37.
[60]Salahifar, E.; Nematollahi, D.; Bayat, M.; Mahyari, A.; Rudbari, H.A. Org. Lett. 2015, 17, 4666.
[61]Tajima, T.; Kishi, Y.; Atsushi, N. Electrochim. Acta 2009, 54, 5959.
[62]Dudkina, Y. B.; Mikhaylov, D. Y.; Gryaznova, T. V.; Tufatullin, A.I.; Kataeva, O. N.; David, A. V.; Budnikova, Y. H. Organometallics2013, 32, 4785.
[63]Dudkina, Y. B.; Gryaznova, T. V.; Sinyashin, O. G.; Budnikova, Y.H. Russ. Chem. Bull. 2015, 64, 1713.
[64]Li, Yi. Q.; Yang, Q. L.; Fang, P.; Mei, T. S.; Zhang, D. Y. Org. Lett.2017, 19, 2905.
[65]Shrestha, A.; Lee, M.; Dunn, A. L.; Sanford, M. S. Org. Lett. 2018,20, 204.
[66]Sauermann,N.;Meyer,T.H.;Tian,C.;Ackermann,L.J.Am.Chem. Soc. 2017, 139, 18452.
[67]Nishiyama, S.; Yamamura, S. Synlett 2002, 533.
[68]Kazuki,M.;Takahashi,M.;Yamamura,S.;Nishiyama,S.Tetrahedron 2001, 57. 5527.
[69]Kawabata,Y.;Naito,Y.;Saitoh,T.;Kawa,K.;Fuchigami,T.;Nishiyama, S. Eur. J. Org. Chem. 2013, 99.
[70]Naito,Y.;Tanabe,T.;Yuki,K.;Ishikawa,Y.;Nishiyama,S.Tetrahedron Lett. 2010, 51, 4776.
[71]Tanabe,T.;Doi,F.;Ogamino,T.;Nishiyama,S.TetrahedronLett.2004, 45, 3477.
[72]Barjau, J.; Schnakenburg, G.; Waldvogel, S. R. Angew. Chem., Int.Ed. 2011, 50, 1415.
[73]Michael, M.; Lars, A.; Caroline, S.; Joaquin, B.; Dieter, S.; Till, O.;Arne, L.; Siegfried, R. W. Eur. J. Org. Chem. 2015, 4876.
[74]Barjau,J.;Schnakenburg,G.;Waldvogel,S.R.Synthesis2011,2054.
[75]Barjau, J.; K?nigs, P.; Kataeva, O.; Waldvogel, S. R.Synlett 2008,2309.
[76]Nematollahi, D.; Tammari, E. J. Org. Chem. 2005, 70, 7769.
[77]Zeng,C.C.;Liu,F.J.;Ping.D.W.;Cai,Y.L.;Zhong,R.G.;Becker, J. Y. J. Electroanal. Chem. 2009, 625, 131.
[78]Zeng, C. C.; Liu, F. J.; Ping, D. W.; Hu, L. M.; Cai, Y. L.; Zhong, R.G.. Tetrahedron 2009, 65, 4505.
[79]Zeng, C. C.; Ping, D. W.; Zhang, S. C.; Zhong, R. G.; Becker, J. Y.J. Electroanal. Chem. 2008, 622, 90.
[80]Khodaei,M.M.;Alizadeh,A.;Pakravan,N.J.Org.Chem.2008,73, 2527.
[81]Fotouhi, L.; Asadi, S.; Tammari, E.; Heravi, M. M.; Nematollahi, D.Anal. Bioanal. Electrochem. 2009, 1, 216.
[82]Amani, A.; Nematollahi, D. J. Org. Chem. 2012, 77, 11130.
[83]Wang, P.; Tang, S.; Huang, P. F.; Lei, A. W. Angew. Chem., Int. Ed.2017, 56, 3009.
[84]Nematollahi, D. N.; Ramazanali, R.; Maryam, M. Synth. Commun.2003, 34, 2269.
[85]Nematollahi,D.;Beiginejad,H.;Varmaghani,F.;Bayat,M.;Salehzadeh, H. J. Electrochem. Soc. 2013, 160, 142.
[86]Zeng,C.C.;Liu,C.F.;Zeng,J.;Zhong,R.G..J.Electroanal.Chem. 2007, 608, 85.
[87]Xiao,H.L.;Yang,C.W.;Zhang,N.T.;Zeng,C.C.;Hu,L.M.;Tian, H. Y.; Little, R. D. Tetrahedron 2013, 69, 658.
[88]Feng, M.L.; Xi,L. Y.; Chen,S. Y.; Yu, X.Q. Eur. J. Org. Chem.2017, 2017, 2746.
[89]Hou, Z. W.; Mao, Z. Y.; Zhao, H. B.; Melcamu, Y. Y.; Lu, X.; Song,J.; Xu, H. C. Angew. Chem., Int. Ed. 2016, 55, 9168.
[90]Hou,Z.W.;Mao,Z.Y.;Song,J.;Xu,H.C.ACSCatal.2017,7,5810.
[91]Wu, Z. J.; Xu, H. C. Angew. Chem., Int. Ed. 2017, 56, 4631.
[92]Xiong, P.; Xu, H.; Song, J. S.; Xu, H. C. J. Am. Chem. Soc. 2018,140, 2460.
[93]Tang, S.; Gao, X. L.; Lei, A. W. Chem. Commun. 2017, 53, 3354.
[94]Wen, J. W.; Shi, W. Y.; Zhang, F.; Liu, D.; Tang, S.; Wang, H. M.;Lin, X. M.; Lei, A. W. Org. Lett. 2017, 19, 3131.
[95]Zhao, H. B.; Hou, Z. W.; Liu, Z. J.; Zhou, Z. F.; Song, J. S.; Xu, H.C. Angew. Chem. Int. Ed. 2017, 56, 587.
[96]Zhao, H. B.; Liu, Z. J.; Song, J.; Xu, H. C. Angew. Chem., Int. Ed.2017, 56, 12732.
[97]Inoue, K.; Ishikawa, Y.; Nishiyama, S. Org. Lett. 2010, 12. 436.
[98]Kajiyama,D.;Inoue,K.;Ishikawa,Y.;Nishiyama,S.Tetrahedron2010, 66, 9779.
[99]Amano, Y.; Inoue, K.; Nishiyama, S. Synlett. 2008, 134.
[100]Morofuji,T.;Shimizu,A.;Yoshida,J.Chem.-Eur.J.2015,21,3211.
[101]Wesenberg, L. J.;Herold, S.; Shimizu, A.; Yoshida, J.; Waldvogel,S. R. Chem.-Eur. J. 2017, 23, 12096.
[102]Xu,F.;Qian,X.Yang.;Li,Y.J.;Xu,H.C.Org.Lett.2017,19,6332.
[103]Tile,G.;Anton,K.;Dieter,S.;Moeller,K.D.;Waldvogel,S.R.Chem. Commun. 2017, 53, 2974.
[104]Tile, G.; Anton, K.; Dieter, S.; Moeller, K. D.; Waldvogel, S. R. J.Am. Chem. Soc. 2017, 139, 12317
[105]Zhang, S.; Li, L. J.; Wang, H. Q.; Li, Q.; Liu, W. M.; Xu. K, Zeng,C. C. Org. Lett. 2018, 20, 252.
[106]Qian,X.Y.;Li,S.Q.;Song,J.S.;Xu,H.C.ACSCatal.2017,7,2730.
[107]Wang, P.; Tang, S.; Lei, A. W. Green Chem. 2017, 19, 2092.
[108]Folgueiras-Amador,A.A.;Qian,X.Y.;Xu,H.C.;Wirth,T.Chem.-Eur. J. 2018, 24, 487.
[109]Chiba, K.; Fukuda, M.; Kim, S.; Kitano, Y.; Tada, M. J. Org. Chem.2000, 31, 7654.
[110]Elseedi, H. R.; Yamamura, S.; Nishiyama, S. Tetrahedron 2002, 58,7485.
[111]Kim,S.;Noda,S.;Hayashi,K.;Chiba,K.Org.Lett.2008,10,1827.
[112]Kim, S.; Hirose, K.; Uematsu, J.; Mikami, Y.; Chiba, K. Chem.-Eur.J. 2012, 18, 6284.
[113]Liu, K.; Tang, S.; Huang, P. F.; Lei, A. W. Nat. Commun. 2017, 8,775.
[114]Tian, C.; Massignan, L.;Meyer, Tjark. H.;Ackermann, L. Angew.Chem., Int. Ed. 2018, 57, 2383.
[115]Xu, F.; Li, Y. Jie.; Huang, C.; Xu, H. C. ACS Catal. 2018, 8, 3820..
[116]Nematollahi,D.;Habibi,D.;Rahmati,M.;Rafiee,M.J.Org.Chem. 2004, 69, 2637.
[117]Hosseiny Davarani, S. S.; Nematollahi, D.; Shamsipur, M.; Najafi,N. M.; Masoumi, L.; Ramyar, S. J. Org. Chem. 2006, 71, 2139.
[118]Salehzadeh, H.; Nematollah, D.; Hesari, H. Green Chem. 2014, 45,2441.
[119]Zeng, C. C.; Liu, F. J.; Ping, D. W.; Hu, L. M.; Cai, Y. L.; Zhong, R.G.. J. Org. Chem. 2010, 41, 6386.
[120]Bai, Y. X.; Ping, D. W.; Little, R. D.; Tian, H. Y.; Hu, L. M.; Zeng,C. C. Tetrahedron 2011, 67, 9334.