CC BY-ND-NC 4.0 · SynOpen 2018; 02(04): 0306-0311
DOI: 10.1055/s-0037-1610400
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Natural Deep Eutectic Solvents as Sustainable Solvents for Suzuki­–Miyaura Cross-Coupling Reactions Applied to Imidazo-Fused Heterocycles

Pierre-Olivier Delaye*
University of Tours, EA 7502 SIMBA, Faculty of Pharmacy, 31 Avenue Monge, Tours, France   eMail: pierre-olivier.delaye@univ-tours.fr
,
Mélanie Pénichon
,
Leslie Boudesocque-Delaye
,
Cécile Enguehard-Gueiffier
,
Alain Gueiffier
› Institutsangaben
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Publikationsverlauf

Received: 11. Oktober 2018

Accepted after revision: 02. November 2018

Publikationsdatum:
27. November 2018 (online)


Abstract

Herein, we present the first Suzuki–Miyaura cross-coupling in a sustainable natural deep eutectic solvent (NaDES) applied to biologically relevant imidazo-fused scaffolds imidazo[1,2-a]pyridine and imidazo[1,2-b]pyridazine. The choline chloride/glycerol (1:2, mol/mol) NaDES allowed the functionalisation of diverse positions on the heterocycles with various boronic acids, by using 2.5 mol% of readily available Pd(OAc)2. Notably, the catalytic system proceeds without any ligands or additives, without protection from the atmosphere.

Supporting Information

 
  • References

    • 1a Enguehard-Gueiffier C, Gueiffier A. Mini-Rev. Med. Chem. 2007; 7: 888
    • 1b Goel R, Luxami V, Paul K. Curr. Top. Med. Chem. 2016; 16: 3590
    • 1c Deep A, Bhatia RK, Kaur R, Kumar S, Jain UK, Singh H, Batra S, Kaushik D, Deb PK. Curr. Top. Med. Chem. 2017; 17: 238
  • 2 Bagdi AK, Santra S, Monir K, Hajra A. Chem. Commun. 2015; 1555
  • 3 Koubachi J, El Kazzouli S, Bousmina M, Guillaumet G. Eur. J. Org. Chem. 2014; 5119
    • 4a Marie E, Boucle S, Enguehard-Gueiffier C, Gueiffier A. Molecules 2012; 17: 10683
    • 4b Henry N, Enguehard-Gueiffier C, Théry I, Gueiffier A. Eur. J. Org. Chem. 2008; 4824
    • 4c Enguehard-Gueiffier C, Croix C, Hervet M, Kazock J.-Y, Gueiffier A, Abarbri M. Helv. Chim. Acta 2007; 90: 2349
    • 4d Enguehard C, Allouchi H, Gueiffier A, Buchwald SL. J. Org. Chem. 2003; 68: 4367
    • 4e Enguehard C, Renou J.-L, Collot V, Hervet M, Rault S, Gueiffier A. J. Org. Chem. 2000; 65: 6572
    • 4f Enguehard C, Hervet M, Allouchi H, Debouzy J.-C, Leger J.-M, Gueiffier A. Synthesis 2001; 4: 595
    • 4g Enguehard C, Allouchi H, Gueiffier A, Buchwald SL. J. Org. Chem. 2003; 68: 5614
  • 5 Zainal-Abidin MH, Hayyan M, Hayya A, Jayakumar NS. Anal. Chim. Acta 2017; 979: 1
    • 6a Ruß C, König B. Green Chem. 2012; 14: 2969
    • 6b Alonso DA, Baeza A, Chinchilla R, Guillena G, Pastor IM, Ramón DJ. Eur. J. Org. Chem. 2016; 612
  • 7 García-Álvarez J. Eur. J. Inorg. Chem. 2015; 5147
    • 8a Imperato G, Höger S, Lenoir D, König B. Green Chem. 2006; 8: 1051
    • 8b Marset X, Khoshnood A, Sotorríos L, Gómez-Bengoa E, Alonso DA, Ramón DJ. ChemCatChem 2017; 9: 1269
  • 9 Ilgen F, König B. Green Chem. 2009; 11: 848
  • 10 Imperato G, Vasold R, König B. Adv. Synth. Catal. 2006; 348: 2243
  • 11 Jérôme F, Ferreira M, Bricout H, Menuel S, Monflier E, Tilloy S. Green Chem. 2014; 16: 3876
  • 12 Punzi A, Coppi DI, Matera S, Capozzi MA. M, Operamolla A, Ragni R, Badudri F, Farinola GM. Org. Lett. 2017; 19: 4754
  • 13 Dilauro G, Garcia SM, Tagarelli D, Vitale P, Perna FM, Capriati V. ChemSusChem 2018; 11: 1
  • 14 Massolo E, Palmieri S, Benaglia M, Capriati V, Perna FM. Green Chem. 2016; 18: 792
    • 15a Dai Y, van Spronsen J, Witkamp G.-J, Verpoorte R, Choi YH. Anal. Chim. Acta 2013; 766: 61
    • 15b Paiva A, Craveiro R, Aroso I, Martins M, Reis RL, Duarte AR. C. ACS Sustainable Chem. Eng. 2014; 2: 1063
  • 16 Kazock J.-Y, Enguehard-Gueiffier C, Théry I, Gueiffier A. Bull. Chem. Soc. Jpn. 2005; 78: 154
  • 17 Zeng J, Tan YJ, Leow ML, Liu X.-W. Org. Lett. 2012; 14: 4386