SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2014 , Vol. 34 >Issue 9: 1743 - 1758

DOI: https://doi.org/10.6023/cjoc201404004

Research Progress on Cross-Coupling with Aryl Diazonium Salts

  • Xuan Shangci ,
  • Wang Xiaodan ,
  • Wang Jianwei ,
  • Zhao Baoli ,
  • Cheng Kai ,
  • Qi Chenze
Expand
  • Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing 312000

Received date: 2014-04-02

  Revised date: 2014-04-24

  Online published: 2014-05-07

Supported by

Project supported by the National Natural Science Foundation of China (No. 21402123), the Zhejiang Provincial Natural Science Foundation of China (No. LQ14B020001), the Science Technology Department of Zhejiang Province (No. 2012R10014-15), the Education Department of Zhejiang Province (No. Y201328443) and the Science Technology Project of Shaoxing City (No. 2013014017).

Fold

Abstract

Aryl diazonium salts have been widely used in cross-coupling reaction due to its easily available and highly reactivity as arylation reagents, which have drawn more and more attention by chemists in organic synthesis in recent years. The research progress since 2006 on cross-coupling with aryl diazonium salts combined with our work is reviewed, focusing on new applications and new progress of aryl diazonium salts in new method to build carbon-carbon bond, with construction of the natural product skeleton, in the field of heterogeneous catalysis and other aspects of green synthesis.

Key words： aryl diazonium salts; cross-coupling; construction of C—C bond; green synthesis

Cite this article

Xuan Shangci , Wang Xiaodan , Wang Jianwei , Zhao Baoli , Cheng Kai , Qi Chenze . Research Progress on Cross-Coupling with Aryl Diazonium Salts[J]. Chinese Journal of Organic Chemistry, 2014 , 34(9) : 1743 -1758 . DOI: 10.6023/cjoc201404004

References

[1] Bonin, H.; Fouquet, E.; Felpin, F.X.Adv.Synth.Catal.2011, 353, 3063.
[2] Li, Y.W.; Yan, X.Y.; Li, X.; Chang, H.-H.; Wei, W.L.Shanxi Chem.Ind.2011, 31, 33.
[3] Taylor, J.G.; Moro, A.V.; Correia, C.R.D.Eur.J.Org.Chem.2011, 1403.
[4] Xiao, Q.; Zhang, Y.; Wang, J.Acc.Chem.Res.2013, 46, 236.
[5] Mo, F.; Dong, G.; Zhang, Y.; Wang, J.Org.Biomol.Chem.2013, 11, 1582.
[6] Roglans, A.; Pla-Quintana, A.; Moreno-Mañas, M.Chem.Rev.2006, 106, 4622.
[7] Cheng, K.; Wang, C.; Ding, Y.; Song, Q.; Qi, C.; Zhang, X.-M.J.Org.Chem.2011, 76, 9261.
[8] Fabrizi, G.; Goggiamani, A.; Sferrazza, A.; Cacchi, S.Angew.Chem., Int.Ed.2010, 49, 4067.
[9] Wu, X.-F.; Neumann, H.; Beller, M.Chem.Commun.2011, 47, 7959.
[10] Panda, B.; Sarkar, T.K.Chem.Commun.2010, 46, 3131.
[11] Wu, X.F.; Schranck, J.; Neumann, H.; Beller, M.Tetrahedron Lett.2011, 52, 3702.
[12] Wu, X.F.; Neumann, H.; Beller, M.Angew.Chem., Int.Ed.2011, 50, 11142.
[13] Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Persiani, D.Org.Lett.2008, 10, 1597.
[14] Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Perboni, A.; Sferrazza, A.; Stabile, P.Org.Lett.2010, 12, 3279.
[15] Robinson, M.K.; Kochurina, V.S.; Hanna, Jr.J.M.Tetrahedron Lett.2007, 48, 7687.
[16] Cepanec, I.; Litvi?, M.; Udikovi?, J.; Pogoreli?, I.; Lovric, M.Tetrahedron 2007, 63, 5614.
[17] Ding, Y.; Cheng, K.; Qi, C.; Song, Q.Tetrahedron Lett.2012, 53, 6269.
[18] Zhou, J.; Yu, S.; Cheng, K.; Qi, C.J.Chem.Res.2012, 11, 672.
[19] Vajpayee, V.; Song, Y.H.; Ahn, J.S.; Chi, K.W.Bull.Korean Chem.Soc.2011, 8, 32.
[20] Zhu, X.; Li, F.; Su, W.Tetrahedron Lett.2013, 54, 1285.
[21] Xia, Z.; Zhu, Q.Org.Lett.2013, 15, 4110.
[22] Saini, V.; Liao, L.; Wang, Q.; Jana, R.; Sigman, M.S.Org.Lett.2013, 15, 5008.
[23] Perez, R.; Veronese, D.; Coelhoband, F.; Antunes, O.Tetrahedron Lett.2006, 47, 1325.
[24] Biajoli, A.F.P.; da Penha, E.T.; Correia, C.R.D.RSC Adv.2012, 2, 11930.
[25] Severino, E.A.; Costenaro, E.R.; Garcia, A.L.L.; Correia, C.R.D.Org.Lett.2003, 5, 305.
[26] Burtoloso, A.C.B.; Garcia, A.L.L.; Miranda, K.C.; Correia, C.R.D.Synlett 2006, 3145.
[27] Meira, P.R.R.; Moro, A.V.; Correia, C.R.D.Synthesis 2007, 2279.
[28] Garcia, A.L.L.; Carpes, M.J.S.; de Oca, A.C.B.M.; dos Santos, M.A.G.; Santana, C.C.; Correia, C.R.D.J.Org.Chem.2005, 70, 1050.
[29] Pastre, J.C.; Correia, C.R.D.Org.Lett.2006, 8,1657.
[30] Silva, K.P.; Godoi, M.N.; Correia, C.R.D.Org.Lett.2007, 15, 2815.
[31] Moro, A.V.; Cardoso, F.S.P.; Correia, C.R.D.Tetrahedron Lett.2008, 49, 5668.
[32] Moro, A.V.; dos Santos, M.R.; Correia, C.R.D.Eur.J.Org.Chem.2011, 7259.
[33] Prediger, P.; Barbosa, L.F.; Génisson, Y.; Correia, C.R.D.J.Org.Chem.2011, 76, 7737.
[34] de Azambuja, F.D.; Correia, C.R.D.Tetrahedron Lett.2011, 52, 42.
[35] da Penha, E.T.; Forni, J.A.; Biajoli, A.F.P.; Correia, C.R.D.Tetrahedron Lett.2011, 52,6342.
[36] Taylor, J.G.; Correia, C.R.D.J.Org.Chem.2011, 76, 857.
[37] Oliveira, C.C.; dos Santos, E.A.F.; Nunes, J.H.B.; Correia, C.R.D.J.Org.Chem.2012, 77, 8182.
[38] Barancelli, D.A.; Salles Jr, A.G.; Taylor, J.G.; Correia, C.R.D.Org.Lett.2012, 14, 6036.
[39] Schwalm, C.S.; Correia, C.R.D.Tetrahedron Lett.2012, 53, 4836.
[40] Correia, C.R.D.; Oliveira, C.C.; Salles Jr, A.G.; Santos, E.A.F.Tetrahedron Lett.2012, 53, 3325.
[41] Schwalm, C.S.; Ilton, B.D.; Castro, D.; Ferrari, J.; Fábio, L.; Oliveira, D.; Aparicio, R.; Correia, C.R.D.Tetrahedron Lett.2012, 53, 1660.
[42] Oliveira, C.C.; Angnes, R.A.; Correia, C.R.D.J.Org.Chem.2013, 78, 4373.
[43] Pastrea, J.C.; Correia, C.R.D.Adv.Synth.Catal.2009, 351, 1217.
[44] Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Sferrazza, A.Synlett 2009, 1277.
[45] Schmidt, B.; Höter, F.; Berger, R.; Jessel, S.Adv.Synth.Catal.2010, 352, 2463.
[46] Felpin, F.X.; Miqueu, K.; Sotiropoulos, J.M.; Fouquet, E.; Ibarguren, O.; Laudien, J.Chem.Eur.J.2010, 16, 5191.
[47] Felpin, F.X.; Barguren, O.; Nassar-Hardy, L.; Fouquet, E.J.Org.Chem.2009, 74, 1349.
[48] Felpin, F.X.; Coste, J.; Zakri, C.; Fouquet, E.; Chem.Eur.J.2009, 15, 7238.
[49] Machado, A.H.L.; de Sousa, M.A.; Patto, D.C.S.; Azevedo, L.F.S.; Bombonato, F.I.; Correia, C.R.D.Tetrahedron Lett.2009, 50, 1222.
[50] Moro, A.V.; Sega, F.; Cardoso, P.; Correia, C.R.D.Org.Lett.2009, 16, 3642.
[51] Soldi, C.; Moro, A.V.; Pizzolatti, M.G.; Correia, C.R.D.Eur.J.Org.Chem.2012, 3607.
[52] Werner, E.W.; Sigman, M.S.J.Am.Chem.Soc.2011, 133, 9692.
[53] Siqueira, F.A.; Taylor, J.G.; Correia, C.R.D.Tetrahedron Lett.2010, 51, 2102.
[54] Nassar-Hardy, L.; Deraedt, C.; Fouquet, E.; Felpin, F.X.Eur.J.Org.Chem.2011, 4616.
[55] Felpin, F.X.; Miqueu, K.; Sotiropoulos, J.M.; Fouquet, E.; Ibarguren, O.; Laudien, J.Chem.Eur.J.2010, 16, 5191.
[56] Yan, M.; Feng, X.Chin.J.Org.Chem.2010, 30, 623.
[57] Yuan, D.; Huang, B.Chin.J.Org.Chem.2012, 32, 1368.
[58] Gallo, V.; Mastrorilli, P.; Nobile, C.; Paolillo, R.; Taccardi, N.Eur.J.Inorg.Chem.2005, 582.
[59] Masllorens, J.; González, I.; Roglans, A.Eur.J.Org.Chem.2007, 158.
[60] Taylor, R.; Felpin, F.X.Org.Lett.2007, 15, 2911.
[61] Qin, Y.; Wei, W.; Luo, M.Synlett 2007, 2410.
[62] Felpin, F.X.; Fouquet, E.Adv.Synth.Catal.2008, 350, 863.
[63] Felpin, F.X.; Fouquet, E.; Zakri, C.Adv.Synth.Catal.2009, 351, 649.
[64] Bonin, H.; Delbrayelle, D.; Demonchaux, P.; Gras, E.Chem.Commun.2010, 46, 2677.
[65] Cacchi, S.; Caponetti, E.; Casadei, M.A.; Giulio, A.D.; Fabrizi, G.; Forte, G.; Goggiamani, A.; Moreno, S.; Paolicelli, P.; Petrucci, F.; Prastaro, A.; Saladino, M.L.Green.Chem.2012, 14, 317.
[66] Felpin, F.X.; Fouquet, E.; Zakri, C.Adv.Synth.Catal.2008, 350, 2559.
[67] Gaikwad, D.; Pore, D.M.Synlett 2012, 2631.
[68] Stern, T.; Rckbrod, S.; Czekelius, C.; Donner, C.; Brunner, H.Adv.Synth.Catal.2010, 352, 1983.
[69] Gholinejad, M.Appl.Organomet.Chem.2013, 27, 19.
[70] Susperregui, N.; Miqueu, K.; Sotiropoulos, J.M.; Callonnec, F.; Fouquet, E.; Felpin, F.X.Chem.Eur.J.2012, 18, 7210.
[71] Ahmed-Omer, B.; Barrow, D.; Wirth, T.Tetrahedron.Lett.2009, 50, 3352.
[72] Zarei, A.; Khazdooz, L.; Hajipour, A.R.; Rafiee, F.; Azizi, G.; Abrishami, F.Tetrahedron Lett.2012, 53, 406.
[73] Bakouri, O.E.; Fernández, M.; Brun, S.; Pla-Quintana, A.; Roglans, A.Tetrahedron 2013, 69, 9761.
[74] Cheng, K.; Zhao, B.; Hu, S.; Zhang, X.-M.; Qi, C.Tetrahedron Lett.2013, 54, 6211.
[75] Wei, S.; Wang, C.; Wang, J.; Cheng, K.Chin.J.Org.Chem.2013, 33, 2402.

Options
Outlines

/

〈 〉