RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2016; 48(23): 4050-4059
DOI: 10.1055/s-0035-1562527
DOI: 10.1055/s-0035-1562527
short review
External-Oxidant-Based Multicomponent Reactions
Weitere Informationen
Publikationsverlauf
Received: 21. Juni 2016
Accepted after revision: 02. Juli 2016
Publikationsdatum:
01. September 2016 (online)
Abstract
This short review covers an innovative approach in multicomponent chemistry involving the employment of an external oxidant. This approach is exploited either to generate one of the reagents of the multicomponent reaction (MCR) or to transform one advanced intermediate into a final stable product. Both aspects are critically analyzed and examples taken from the recent literature are discussed in detail.
1 Introduction
2 Generation of One Reactant through an Oxidative Process
2.1 Passerini Reactions
2.2 Ugi-Type Reactions
2.3 Other Multicomponent Reactions
3 Oxidation of an Advanced Intermediate as a Driving Process
3.1 Aromatization of a Reaction Intermediate
3.2 Oxidation of an Advanced Intermediate without Aromatization
4 Conclusions
-
References
- 1 Cioc RC, Ruijter E, Orru RV. A. Green Chem. 2014; 16: 2958
- 2 Garbarino S, Ravelli D, Protti S, Basso A. Angew. Chem. Int. Ed. 2016; in press; DOI: 10.1002/ange.201605288
- 3 Orru RV. A, Ruijter E In Topics in Heterocyclic Chemistry . Vol. 23. Maes BU. W. Springer-Verlag; Berlin: 2010
- 4 Multi-Component and Sequential Reactions in Polymer Synthesis – Advances in Polymer Science. Vol. 269. Theato P. Springer International Publishing; Cham: 2015
- 5 Ngouansavanh T, Zhu JP. Angew. Chem. Int. Ed. 2006; 45: 3495
- 6 Leon F, Rivera DG, Wessjohann LA. J. Org. Chem. 2008; 73: 1762
- 7 Henze M, Kreye O, Brauch S, Nitsche C, Naumann K, Wessjohann LA, Westermann B. Synthesis 2010; 2997
- 8a De Moliner F, Crosignani S, Banfi L, Riva R, Basso A. J. Comb. Chem. 2010; 12: 613
- 8b De Moliner F, Crosignani S, Galatini A, Riva R, Basso A. ACS Comb. Sci. 2011; 13: 453
- 9 Kan X.-W, Deng X.-X, Du F.-S, Li Z.-C. Macromol. Chem. Phys. 2014; 215: 2221
- 10 Brioche J, Masson G, Zhu JP. Org. Lett. 2010; 12: 1432
- 11 For an example of aldehyde oxidation in a Passerini reaction, see: Li M, Qiu B, Kong X.-J, Wen L.-R. Org. Chem. Front. 2015; 2: 1326
- 12 Karimi B, Farhangi E. Adv. Synth. Catal. 2013; 355: 508
- 13 Moni L, Banfi L, Basso A, Carcone L, Rasparini M, Riva R. J. Org. Chem. 2015; 80: 3411
- 14 De Moliner F, Bigatti M, Banfi L, Riva R, Basso A. Org. Lett. 2014; 16: 2280
- 15 Moni L, Banfi L, Basso A, Martino E, Riva R. Org. Lett. 2016; 18: 1638
- 16 Adib M, Sheikhi E, Azimzadeh M. Tetrahedron Lett. 2015; 56: 1933
- 17 Kornblum N, Jones WJ, Anderson GJ. J. Am. Chem. Soc. 1959; 81: 4113
- 18 Drouet F, Masson G, Zhu JP. Org. Lett. 2013; 15: 2854
- 19 Khan IA, Saxena AK. Tetrahedron 2012; 68: 294
- 20 Shaabani A, Shaabani Z, Badali E. RSC Adv. 2015; 5: 91966
- 21 Ngouansavanh T, Zhu JP. Angew. Chem. Int. Ed. 2007; 46: 5775
- 22 Islas-Jacome A, Gutierrez-Carrillo A, Garcia-Garibay MA, Gonzalez-Zamora E. Synlett 2014; 25: 403
- 23 de Graaff C, Bensch L, van Lint MJ, Ruijter E, Orru RV. A. Org. Biomol. Chem. 2015; 13: 10108
- 24 El Kaïm L, Grimaud L, Oble J, Wagschal S. Tetrahedron Lett. 2009; 50: 1741
- 25 Jiang G, Chen J, Huang JS, Che CM. Org. Lett. 2009; 11: 4568
- 26 Rueping M, Vila C. Org. Lett. 2013; 15: 2092
- 27 Rueping M, Vila C, Bootwicha T. ACS Catal. 2013; 3: 1676
- 28 Chen Y, Feng G. Org. Biomol. Chem. 2015; 13: 4260
- 29a Ye X, Xie C, Pan Y, Han L, Xie T. Org. Lett. 2010; 12: 4240
- 29b Ye X, Xie CS, Huang R, Liu JH. Synlett 2012; 23: 409
- 29c Xie C, Han L. Tetrahedron Lett. 2014; 55: 240
- 30 Dighe SU, Kolle S, Batra S. Eur. J. Org. Chem. 2015; 4238
- 31 Ramesha AB, Raghavendra GM, Nandeesh KN, Rangappa KS, Mantelingu K. Tetrahedron Lett. 2013; 54: 95
- 32a Garima, Srivastava VP, Yadav LD. S. Tetrahedron Lett. 2010; 51: 6436
- 32b Revanna CN, Raghavendra GM, Vijay TA. J, Rangappa KS, Badregowda DG, Mantelingu K. Chem. Lett. 2014; 43: 178
- 33 Harris GH, Graham AE. Tetrahedron Lett. 2010; 51: 6890
- 34 Gualtierotti JB, Schumacher X, Fontaine P, Masson G, Wang Q, Zhu JP. Chem. Eur. J. 2012; 18: 14812
- 35 Movahed SK, Lehi NF, Dabiri M. RSC Adv. 2014; 4: 42155
- 36 Han Z, Zhang L, Li Z, Fan R. Angew. Chem. Int. Ed. 2014; 53: 6805
- 37 Potowski M, Merten C, Antonchick AP, Waldmann H. Chem. Eur. J. 2015; 21: 4913
- 38 Li SY, Wu J. Org. Lett. 2011; 13: 712
- 39 Lieby-Muller F, Allais C, Constantieux T, Rodriguez J. Chem. Commun. 2008; 4207
- 40 Barbe G, Charette AB. J. Am. Chem. Soc. 2008; 130: 18
- 41 Allais C, Constantieux T, Rodriguez J. Chem. Eur. J. 2009; 15: 12945
- 42 Allais C, Lieby-Muller F, Constantieux T, Rodriguez J. Adv. Synth. Catal. 2012; 354: 2537
- 43 Zhu C, Bi B, Ding Y, Zhang T, Chen Q.-Y. Org. Biomol. Chem. 2015; 13: 6278
- 44 Heravi MM, Behbahani FK, Oskooie HA, Shoar RH. Tetrahedron Lett. 2005; 46: 2775
- 45 Heravi MM, Baghernejad B, Oskooie HA. Tetrahedron Lett. 2009; 50: 767
- 46 Cho Y.-H, Lee C.-Y, Cheon C.-H. Tetrahedron 2013; 69: 6565
- 47 Cho Y.-H, Kim K.-H, Cheon C.-H. J. Org. Chem. 2014; 79: 901
- 48 Bouma MJ, Masson G, Zhu JP. Eur. J. Org. Chem. 2012; 475
- 49a Lalli C, Bouma MJ, Bonne D, Masson G, Zhu J. Chem. Eur. J. 2011; 17: 880
- 49b Bonne D, Dekhane M, Zhu J. Angew. Chem. Int. Ed. 2007; 46: 2485
- 50 Dragan V, McWilliams JC, Miller R, Sutherland K, Dillon JL, O’Brien MK. Org. Lett. 2013; 15: 2942
- 51 Fontaine P, Chiaroni A, Masson G, Zhu J. Org. Lett. 2008; 10: 1509
- 52 Yan H, Yan RL, Yang SZ, Gao X, Wang YL, Huang GS, Liang YM. Chem. Asian J. 2012; 7: 2028
- 53 Jiang Q, Wang J.-Y, Guo C. J. Org. Chem. 2014; 79: 8768