2.4 Silicon-Mediated Multicomponent Reactions

J. Wan

doi:10.1055/sos-SD-211-00135

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Müller, T. J. J.: 2014 Science of Synthesis, 2013/6: Multicomponent Reactions, Volume 2 DOI: 10.1055/sos-SD-211-00135

Multicomponent Reactions, Volume 2

2.4 Silicon-Mediated Multicomponent Reactions

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Editor: Müller, T. J. J.

Authors: Alavijeh, N. S.; Arndtsen, B. A.; Balalaie, S.; Bonne, D.; Chen, C.; Coquerel, Y.; Elliott, M.; Festa, A.; Fusano, A.; Ghabraie, E.; Jones, D. H.; Modha, S.; Müller, T. J. J.; Purushothaman, S.; Raghunathan, R.; Rodriguez, J.-A.; Ryu, I.; Sarvary, A.; Shaabani, A.; Shaabani, S.; Szabó, K. J.; Takasu, K.; Tjutrins, J.; Van der Eycken, E.; Voskressensky, L.; Wan, J.; Xi, C.

Title: Multicomponent Reactions, Volume 2

Subtitle: Reactions Involving an α,α-Unsaturated Carbonyl Compound as Electrophilic Component, Cycloadditions, and Boron-, Silicon-, Free-Radical-, and Metal-Mediated Reactions

Print ISBN: 9783131728319; Online ISBN: 9783132064317; Book DOI: 10.1055/b-003-125831

1st edition © 2014. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Multicomponent Reactions

Science of Synthesis Reference Libraries

Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Carreira, E. M.; Decicco, C. P.; Fürstner, A.; Molander, G.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.

Type: Multivolume Edition

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Abstract

Silicon reagents are commonly employed in organic synthesis as catalysts or promoters because of their availability and versatile catalytic activity. Some typical silicon reagents, such as trimethylsilyl halides (where the halide is chlorine or iodine) or trimethylsilyl trifluoromethanesulfonate, are known to be capable of acting as Lewis acids, Brønsted acids (upon hydrolysis), and water scavengers. This section presents an overview of the particularly broad application of silicon reagents in multicomponent reactions. Silicon-mediated multicomponent processes that lead to both cyclic and acyclic products are summarized.

Key words

Biginelli reactions - cyclization reactions - 1,3-dicarbonyl compounds - imidazoles - pyridine synthesis - quinoxalines - silicon reagents - tetrahydropyridinones - 1,3-thiazines

1 Dilman AD, Ioffe S. Chem. Rev. 2003; 103: 733

PubMed Search in Google Scholar

2 Wan J.-P, Liu Y. Curr. Org. Chem. 2011; 15: 2758

Search in Google Scholar

3 Volochnyuk DM, Ryabukhin SV, Plaskon AS, Grygorenko OO. Synthesis 2009; 3719

4 Multicomponent Reactions. Zhu J, Bienaymé H. Wiley-VCH; Weinheim, Germany 2005

Crossref Search in Google Scholar

5 Dömling A. Chem. Rev. 2006; 106: 17

PubMed Search in Google Scholar

6 Ugi I. Pure Appl. Chem. 2001; 73: 187

Search in Google Scholar

7 Touré BB, Hall DG. Chem. Rev. 2009; 109: 4439

PubMed Search in Google Scholar

8 DʼSouza DM, Müller TJJ. Chem. Soc. Rev. 2007; 36: 1095

PubMed Search in Google Scholar

9 Biginelli P. Gazz. Chim. Ital. 1893; 23: 360

Search in Google Scholar

10 Sabitha G, Kiran Kumar Reddy GS, Reddy CS, Yadav JS. Synlett 2003; 858

11 Zhu Y, Pan Y, Huang S. Synth. Commun. 2004; 34: 3167

Search in Google Scholar

12 Pisani L, Prokopcová H, Kremsner JM, Kappe CO. J. Comb. Chem. 2007; 9: 415

PubMed Search in Google Scholar

13 Matloobi M, Kappe CO. J. Comb. Chem. 2007; 9: 275

PubMed Search in Google Scholar

14 Kremsner JM, Stadler A, Kappe CO. J. Comb. Chem. 2007; 9: 285

PubMed Search in Google Scholar

15 Bose DS, Kumar RK, Fatima L. Synlett 2004; 279

16 Ryabukhin SV, Plaskon AS, Ostapchuk EN, Volochnyuk DM, Tolmachev AA. Synthesis 2007; 417

17 Zhu Y, Pan Y, Huang S. Heterocycles 2005; 65: 133

Search in Google Scholar

18 Wang Z.-T, Xu L.-W, Xia C.-G, Wang HQ. Tetrahedron Lett. 2004; 45: 7951

Search in Google Scholar

19 Wang Z.-T, Xu L.-W, Xia C.-G, Wang HQ. Tetrahedron Lett. 2006; 47: 1361

Search in Google Scholar

20 Sabitha G, Reddy KB, Srinivas R, Yadav JS. Helv. Chim. Acta 2005; 88: 2996

Search in Google Scholar

21 Zhu Y.-l, Huang S.-l, Pan Y.-j. Eur. J. Org. Chem. 2005; 2354

22 Kefayati H, Fakhriyannejad M, Mohammadi AA. Phosphorus, Sulfur Silicon Relat. Elem. 2009; 184: 1796

Search in Google Scholar

23 Wan J.-P, Pan Y.-J. Chem. Commun. (Cambridge) 2009; 2768

PubMed

24 Ryabukhin SV, Plaskon AS, Ostapchuk EN, Volochnyuk DM, Shishkin OV, Tolmachev AA. J. Fluorine Chem. 2008; 129: 625

Search in Google Scholar

25 Azizian J, Mirza B, Mojtahedi MM, Abaee MA, Sargordan M. J. Fluorine Chem. 2008; 129: 1083

Search in Google Scholar

26 Zhu Y, Huang S, Wan J, Yan L, Pan Y, Wu A. Org. Lett. 2006; 8: 2599

PubMed Search in Google Scholar

27 Sasada T, Sakai N, Konakahara T. J. Org. Chem. 2008; 73: 6905

PubMed Search in Google Scholar

28 Wan J.-P, Gan S.-F, Sun G.-L, Pan Y.-J. J. Org. Chem. 2009; 74: 2862

PubMed Search in Google Scholar

29 Sharma V, Tepe JJ. Org. Lett. 2005; 7: 5091

PubMed Search in Google Scholar

30 Krasavin M, Tsirulnikov S, Nikulnikov M, Kysil V, Ivachtchenko A. Tetrahedron Lett. 2008; 49: 5241

Search in Google Scholar

31 Krasavin M, Shkavrov S, Parchinsky V, Bukhryakov K. J. Org. Chem. 2009; 74: 2627

PubMed Search in Google Scholar

32 Kysil V, Tkachenko S, Khvat A, Williams C, Tsirulnikov S, Churakova M, Ivachtchenko A. Tetrahedron Lett. 2007; 48: 6239

Search in Google Scholar

33 Kysil V, Khvat A, Tsirulnikov S, Tkachenko S, Williams C, Churakova M, Ivachtchenko A. Eur. J. Org. Chem. 2010; 1525

34 Kysil V, Khvat A, Tsirulnikov S, Tkachenko S, Ivachtchenko A. Tetrahedron Lett. 2009; 50: 2854

Search in Google Scholar

35 Sabitha G, Kiran Kumar Reddy GS, Reddy CS, Yadav JS. Tetrahedron Lett. 2003; 44: 4129

Search in Google Scholar

36 Ryabukhin SV, Plaskon AS, Ostapchuk EN, Volochnyuk DM, Shishkin OV, Shivanyuk AN, Tolmachev AA. Org. Lett. 2007; 9: 4215

PubMed Search in Google Scholar

37 Mao H, Wan J, Pan Y. Tetrahedron 2009; 65: 1026

Search in Google Scholar

38 Heravi MM, Ranjbar L, Derikvand F, Bamoharram FF. J. Mol. Catal. A: Chem. 2007; 271: 28

Search in Google Scholar

39 Salama TA, Elmorsy SS, Khalil A.-GM, Ismail MA. Tetrahedron Lett. 2007; 48: 6199

Search in Google Scholar

40 Yang B.-L, Wang Z.-T, Yang S.-J, Tian S.-K. Chem.–Eur. J. 2010; 16: 718

PubMed Search in Google Scholar

41 Saidi MR, Azizi N. Tetrahedron: Asymmetry 2002; 13: 2523

Search in Google Scholar

42 Saidi MR, Azizi N. Tetrahedron: Asymmetry 2003; 14: 389

Search in Google Scholar

43 Mekhalfia A, Markó IE. Tetrahedron Lett. 1991; 32: 4779

Search in Google Scholar

44 Tietze LF, Schiemann K, Wegner C, Wulff C. Chem.–Eur. J. 1996; 2: 1164

Search in Google Scholar

45 Wang MW, Chen YJ, Wang D. Synlett 2000; 385

46 Saidi MR, Azizi N. Synlett 2002; 1347

47 Li H.-H, Dong D.-J, Tian S.-K. Eur. J. Org. Chem. 2008; 3623