Synthesis of Oxindoles by Eosin Y Catalyzed under Visible Light
- Corresponding author: Zhang Ronghua, rhzhang@tongji.edu.cn
Citation:
Tian Wenyan, Xu Song, Liang Zhongwei, Sun Deli, Zhang Ronghua. Synthesis of Oxindoles by Eosin Y Catalyzed under Visible Light[J]. Chinese Journal of Organic Chemistry,
;2016, 36(9): 2121-2129.
doi:
10.6023/cjoc201603002
Yang, F.;Klumphu, P.;Liang, Y.M.; Lipshutz, B.H.Chem.Commun.2014, 50, 936.
(b) Meng, Y.;Guo, L.N.; Wang, H.;Duan, X.H.Chem.Commun.2013, 49, 7540.
(c) Wang, H.;Guo, L.N.; Duan, X.H.Adv.Synth.Catal.2013, 355, 2222.
(d) Wang, S.C.; Huang, X.H.; Li, B.W.; Ge, Z.M.; Wang, X.;Li, R.T.Tetrahedron 2015, 71, 1869.
Ciamician, G.Science 1912, 36, 385.
(b) Zeitler, K.Angew.Chem., Int.Ed.2009, 48, 9785.
(c) Yoon, T.P.; Ischay, M.A.; Du, J.Nat.Chem.2010, 2, 527.
(d) Narayanam, J.M.R.; Stephenson, C.R.J.Chem.Soc.Rev.2011, 40, 102.
(e) Xuan, J.;Xiao, W.J.Angew.Chem., Int.Ed.2012, 51, 6828.
(f) Schultz, D.M.; Yoon, T.P.Science 2014, 343, 985.
Shih, H.W.; Vander Wal, M.N.; Grange, R.L.; MacMillan, D.W.C.J.Am.Chem.Soc.2010, 132, 13600.
(b) Noble, A.;MacMillan, D.W.C.J.Am.Chem.Soc.2014, 136, 11602.
(c) Prier, C.K.; MacMillan, D.W.C.Chem.Sci.2014, 5, 4173.
(d) Jeffrey, J.L.; Petronijevic, F.R.; MacMillan, D.W.C.J.Am.Chem.Soc.2015, 137, 8404.
Ischay, M.A.; Anzovino, M.E.; Du, J.;Yoon, T.P.J.Am.Chem.Soc.2008, 130, 12886.
(b) Du, J.;Yoon, T.P.J.Am.Chem.Soc.2009, 131, 14604.
(c) Ischay, M.A.; Lu, Z.;Yoon, T.P.J.Am.Chem.Soc.2010, 132, 8572.
(d) Lu, Z.;Parrish, J.D.; Yoon, T.P.Tetrahedron 2014, 70, 4270.
Dai, C.H.; Narayanam, J.M.R; Stephenson, C.R.J.Nat.Chem.2011, 3, 140.
(b) Narayanam, J.M.R.; Tucker, J.W.; Stephenson, C.R.J.J.Am.Chem.Soc.2009, 131, 8756.
Furst, L.;Matsuura, B.S.; Narayanam, J.M.R.; Tucker, J.W.; Stephenson, C.R.J.Org.Lett.2010, 12, 3104.
(b) Neumann, M.;Fldner, S.;Konig, B.;Zeitler, K.Angew.Chem., Int.Ed.2011, 50, 951.
(c) Liu, Q.;Yi, H.;Liu, J.;Yang, Y.H.; Zhang, X.;Zeng, Z.Q.; Lei, A.W.Chem.-Eur.J.2013, 19, 5120.
(d) Jadhav, S.D.; Bakshi, D.;Singh, A.J.Org.Chem.2015, 80, 10187.
Xie, J.;Xu, P.;Li, H.M.; Xue, Q.C; Jin, H.M.; Cheng, Y.X; Zhu, C.J.Chem.Commun.2013, 49, 5672.
(b) Xu, P.;Xie, J.;Xue, Q.C.; Pan, C.D.; Cheng, Y.X.; Zhu, C.J.Chem.-Eur.J.2013, 19, 14039.
(c) Tang, X.J.; Thomoson, C.S.; Dolbier, W.R., Jr.Org.Lett.2014, 16, 4594.
(d) Fu, W.J.; Zhu, M.;Zou, G.L.; Xu, C.;Wang, Z.Q.Synlett 2014, 25, 2513.
(e) Fu, W.J.; Xu, F.J.; Fu, Y.Q.; Zhu, M.;Yu, J.Q.; Xu, C.;Zou, D.P.J.Org.Chem.2013, 78, 12202.
(f) Fu, W.;Zhu, M.;Zou, G.;Xu, C.;Wang, Z.Asian J.Org.Chem.2014, 3, 1273.
(g) Xia, D.;Miao, T.;Li, P.-H.; Wang, L.Chem.Asian J.2015, 10, 1919.
Liu, H.J.; Feng, W.;Kee, C.W.; Zhao, Y.J.; Leow, D.S.; Pan, Y.H.; Tan, C.H.Green Chem.2010, 12, 953.
(b) Hari, D.P.; Konig, B.Org.Lett.2011, 13, 3852.
(c) Neumann, M.;Fuldner, S.;Konig, B.;Zeitler, K.Angew.Chem., Int.Ed.2011, 50, 951.
(d) Hari, D.P.; Konig, B.Chem.Commun.2014, 50, 6688.
(e) Liang, Z.W.; Xu, S.;Tian, W.Y.; Zhang, R.H.Beilstein J.Org.Chem.2015, 11, 425.
Neckers, D.C.; Aguilera, O.M.V.; Wolff, T.Advances in Photochemistry, John Wiley&Sons Inc, 1993, Vol.18, p.315.
(b) Encinas, M.V.; Rufs, A.M.; Bertolotti, S.G.; Previtali, C.M.Polymer 2009, 50, 2762.
(c) Lazarides, T.;McCormick, T.;Du, P.W.; Luo, G.G.; Lindley, B.;Eisenberg, R.J.Am.Chem.Soc.2009, 131, 9192.
(d) Lee, S.H.; Nam, D.H.; Park, C.B.Adv.Synth.Catal.2009, 351, 2589.
Zhang, M.;Chen, C.C.; Ma, W.H.; Zhao, J.C.Angew.Chem., Int.Ed.2008, 47, 9730.
(b) Majek, M.;Filace, F.;Wangelin, A.J.V.Beilstein J.Org.Chem.2014, 10, 981.
(c) Majek, M.;Wangelin, A.J.V.Angew.Chem., Int.Ed.2015, 54, 2270.
Fabry, D.C.; Stodulski, M.;Hoerner, S.;Gulder, T.Chem.Eur.J.2012, 18, 10834.
doi: 10.1002/chem.201201232
Wang, S.C.; Huang, X.H.; Li, B.W.; Ge, Z.M.; Wang, X.;Li, R.T.Tetrahedron 2015, 71, 1869.
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