Synthesis 2015; 47(16): 2385-2390
DOI: 10.1055/s-0034-1380719
special topic
© Georg Thieme Verlag Stuttgart · New York

Toward a Green Atom Economy: Development of a Sustainable Multicomponent Reaction

Silvia Garbarino
a   Bioorganic Chemistry Group, Department of Chemistry and Industrial Chemistry, University of Genova, Via Dodecaneso 31, 16146 Genova, Italy   Email: andrea.basso@unige.it
,
Stefano Protti*
b   PhotoGreen Lab, Department of Chemistry University of Pavia, Viale Taramelli 12, 27100 Pavia, Italy   Email: prottistefano@gmail.com
,
Andrea Basso*
a   Bioorganic Chemistry Group, Department of Chemistry and Industrial Chemistry, University of Genova, Via Dodecaneso 31, 16146 Genova, Italy   Email: andrea.basso@unige.it
› Author Affiliations
Further Information

Publication History

Received: 19 March 2015

Accepted after revision: 13 April 2015

Publication Date:
26 May 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.

 
  • 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

    • For recent examples, see:
    • 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

    • For reviews, see:
    • 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