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Synthesis 2015; 47(16): 2385-2390
DOI: 10.1055/s-0034-1380719
DOI: 10.1055/s-0034-1380719
special topic
Toward a Green Atom Economy: Development of a Sustainable Multicomponent Reaction
Weitere Informationen
Publikationsverlauf
Received: 19. März 2015
Accepted after revision: 13. April 2015
Publikationsdatum:
26. Mai 2015 (online)
Abstract
The recently discovered photoinduced three-component reaction of diazo ketones, carboxylic acids, and isocyanides can be efficiently performed under continuous-flow conditions with consequential advantages in terms of selectivity and productivity. The investigation of the flow process and the determination of its sustainability are discussed in detail. This multicomponent reaction affords stereodefined captodative olefins, useful as synthons in organic chemistry.
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References
- 1a Biggs-Houck JE, Younai A, Shaw JT. Curr. Opin. Chem. Biol. 2010; 14: 371
- 1b Ruijter E, Scheffelaar R, Orru RV. A. Angew. Chem. Int. Ed. 2011; 50: 6234
- 2a Cioc RC, Ruijter E, Orru RV. A. Green Chem. 2014; 16: 2958
- 2b Ganem B. Acc. Chem. Res. 2009; 42: 463
- 2c Andraos J. ACS Sustainable Chem. Eng. 2013; 1: 496
- 3 Jiang B, Shi F, Tu S.-J. Curr. Org. Chem. 2010; 14: 357
- 4a Kalpogiannaki D, Martini C.-I, Nikopoulou A, Nyxas JA, Pantazi V, Hadjiarapoglou LP. Tetrahedron 2013; 69: 1566
- 4b Rueping M, Vila C. Org. Lett. 2013; 15: 2092
- 4c Rueping M, Vila C, Bootwicha T. ACS Catal. 2013; 3: 1676
- 5 Protti S, Dondi D, Fagnoni M, Albini A. Green Chem. 2009; 11: 239
- 6a Basso A, Banfi L, Garbarino S, Riva R. Angew. Chem. Int. Ed. 2013; 52: 2096
- 6b Garbarino S, Banfi L, Riva R, Basso A. J. Org. Chem. 2014; 79: 3615
- 7a Kirmse W. Eur. J. Org. Chem. 2002; 2193
- 7b Meier H, Zeller K.-P. Angew. Chem. Int. Ed. Engl. 1975; 14: 32
- 7c La Spisa F, Tron GC, El Kaïm L. Synthesis 2014; 46: 829
- 8a Lasri J, Mukhopadhyay S, Charmier MA. J. J. Heterocycl. Chem. 2008; 45: 1385
- 8b Döpp D. In Organic, Physical, and Materials Photochemistry . Ramamurthy V, Schanze KS. Marcel Dekker; New York: 2000. Chap. 3, 101
- 9 Basso A, Banfi L, Riva R. Molecules 2011; 16: 8775
- 10a Birkhofer H, Hädrich J, Beckhaus HD, Rüchardt C. Angew. Chem. Int. Ed. 1987; 26: 573
- 10b Stella L, Harvey JN. In Radicals in Organic Synthesis . Renaud P, Sibi MP. Wiley-VCH; Weinheim: 2001. Chap. 3.3, 360
- 11 Arai T, Tokumaru K. Chem. Rev. 1993; 93: 23
- 12a Coyle EE, Oelgemöller M. Photochem. Photobiol. Sci. 2008; 7: 1313
- 12b Su Y, Straathof NJ. W, Hessel V, Noël T. Chem. Eur. J. 2014; 20: 10562
- 12c Knowles JP, Elliott LD, Booker-Milburn KI. Beilstein J. Org. Chem. 2012; 8: 2025
- 12d Elliott LD, Knowles JP, Koovits PJ, Maskill KG, Ralph MJ, Lejeune G, Edwards LJ. Robinson R. I, Clemens IR, Cox B, Pascoe DD, Koch G, Eberle M, Berry MB, Booker-Milburn KI. Chem. Eur. J. 2014; 20: 15226
- 13 Burdzinski G, Platz MS. J. Phys. Org. Chem. 2010; 23: 308
- 14 Jimenez-Gonzalez C, Ponder CS, Broxterman QB, Manley JB. Org. Process Res. Dev. 2011; 15: 912
- 15 Ravelli D, Protti S, Fagnoni M, Albini A. Curr. Org. Chem. 2013; 17: 2366
- 16 See for example: Ravelli D, Protti S, Neri P, Fagnoni M, Albini A. Green Chem. 2011; 13: 1876
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