Synthesis 2022; 54(20): 4608-4614
DOI: 10.1055/s-0040-1720029
paper

An Efficient CuI-Catalyzed C–S Cross-Coupling Reaction under Microwave Irradiation in DMF

Rakhi Katla
a   Organic Catalysis and Biocatalysis Laboratory - LACOB, Federal University of Grande Dourados-UFGD, Dourados/MS, Brazil
,
Ramesh Katla
b   Foreign Visiting Professor, Organic Chemistry Laboratory-4, School of Chemistry and Food, Federal University of Rio Grande-FURG, Rio Grande, RS-Brazil
,
a   Organic Catalysis and Biocatalysis Laboratory - LACOB, Federal University of Grande Dourados-UFGD, Dourados/MS, Brazil
› Author Affiliations


Abstract

Microwave irradiated C–S cross-coupling reaction to synthesize 5-aryllthiobenzo-2,1,3-thiadiazole derivatives from a variety of benzene thiols with 5-bromo-2,1,3-benzothiadiazole, catalyzed by Cu(I) iodide and potassium carbonate as a cost-effective base in DMF, was conducted, affording excellent yields of the desired products. Microwave conditions assisted in the development of C–S cross-coupling reaction with higher yields.

Supporting Information



Publication History

Received: 03 April 2022

Accepted after revision: 27 May 2022

Article published online:
05 July 2022

© 2022. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
  • References

  • 1 Gawande MB, Shelke SN, Zboril R, Varma RS. Acc. Chem. Res. 2014; 47: 1338
  • 2 Hoz AD. L, Ortiza AD, Prieto P. In Alternative Energy Sources for Green Chemistry . Stefanidis G, Stankiewicz A. Royal Society of Chemistry; Cambridge: 2016: 1-33
  • 3 For a recent review on the use of microwave irradiation, see: Appukkuttan P, Van der Eycken E. Eur. J. Org. Chem. 2008; 1133
  • 4 Appukkuttan P, Mehta VP, Van der Eycken E. Chem. Soc. Rev. 2010; 39: 1467
    • 5a For recent review on nano-catalysis, see: Polshettiwar V, Varma RS. Green Chem. 2010; 12: 743
    • 5b Polshettiwar V, Nadagouda MN, Varma RS. Aust. J. Chem. 2009; 62: 16
  • 6 For an excellent review, see: Bogdal D, Penczek P, Pielichowski J, Prociak A. Adv. Polym. Sci. 2003; 163: 193
    • 7a Mahajan K, Fahmi N, Singh RV. Indian J. Chem., Sect. A: Inorg., Bio-Inorg., Phys.,Theor. Anal. Chem. 2007; 46: 1221
    • 7b Mohanan K, Kumari S, Rijulal G. J. Rare Earths 2008; 26: 16
  • 8 Duan W, Huang J, Kowalski JA, Shkrob IA, Vijayakumar M, Walter E, Wei X. ACS Energy Lett. 2017; 2: 1156
  • 9 Wang Y, Michinobu T. J. Mater. Chem. C. 2016; 4: 6200
  • 10 Neto BA. D, Lapis AA. M, da Silva JE. N, Dupont J. Eur. J. Org. Chem. 2013; 228
  • 11 Frizon TE. A, Valdivia M, Westrup JC, da Costa Duarte R, Zapp E, Domiciano KG, Rodembusch FS, Dal-Bó AG. Dyes Pigments 2016; 135: 26
  • 12 Sukhikh T, Ogienko D, Bashirov D, Konchenkoa S. Russ. Chem. Bull. 2019; 68: 651
  • 13 Kukreja G, Phukan S, Kodam J, More DM, Uravane MV, Palle VP, Kamboj RK. Patent WO2013005157 A1, 2013
  • 14 Balaguez RA, Ricordi VG, Duarte RC, Toldo JM, Santos CM, Schneider PH, Gonçalves PF. B, Rodembusch FS, Alves D. RSC Adv. 2016; 6: 49613
  • 15 Santos BF, Pereira CF, Pinz MP, Oliveira AR, Brand G, Katla R, Domingues NL. C. Appl. Organomet. Chem. 2020; e5650
    • 16a Katla R, Katla R, da Silva CD. G, dos Santos BF, Branquinho TA, Ferro CT. B, Domingues NL. C. ChemistrySelect 2019; 4: 1
    • 16b de Oliveira AR, da Silva CD. G, Katla R, Rocha MP. D, Albuquerque TB, Kupfer VL, Rinaldi AW, Domingues NL. C. ChemistrySelect 2017; 2: 4462
    • 16c Katla R, Chowrasia R, da Silva CD. G, de Oliveira AR, dos Santos BF, Domingues NL. C. Synthesis 2017; 49: 5143
    • 16d Katla R, Chowrasia R, Manjari PS, da Silva CD. G, dos Santos BF, Domingues NL. C. New J. Chem. 2016; 40: 9471
    • 16e Chowrasia R, Katla R, Rocha MP. D, Branquinho TA, de Oliveira AR, Manjari PS, Domingues NL. C. Tetrahedron Lett. 2016; 57: 1656
    • 16f de Oliveira AR, Katla R, Rocha MP. D, Albuquerque TB, da Silva CD. G, Kupfer VL, Rinaldi AW, Domingues NL. C. Synthesis 2016; 48: 4489
    • 16g Katla R, Chowrasia R, Manjari PS, Domingues NL. C. RSC Adv. 2015; 5: 41716
  • 17 Rout L, Saha P, Jammi S, Punniyamurthy T. Eur. J. Org. Chem. 2008; 640