Nermin BİRİCİK, Nermin MERİÇ, Cezmi KAYAN, Bahattin GÜMGÜM, Zeynep ÖZGEN, Sevil ŞEKER AZİZOĞLU

7985

Synthesis of new thiol-derivatized aminophosphines and their catalytic activities in C{C coupling reactions

Synthesis of new thiol-derivatized aminophosphines and their catalytic activities in C{C coupling reactions

A series of new aminophosphines [Ph 2 PHN-C 6 H 4 -R, where R = o -SH ( 4a ), m -SH ( 4b) or p -SH ( 4c )] were readily synthesized from cheap starting materials by the phosphorylation reaction of o , m , and p -aminothiophenols with Ph 2 PCl in the presence of triethyl amine. The new compounds were characterized by NMR and IR spectroscopy and microanalysis. In addition, aminophosphine ligands{palladium systems were investigated as precatalysts in C{C coupling reactions. Compounds 4b and 4c were proved to be excellent catalysts for Suzuki and Heck cross-coupling reactions.
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  • 1. Dewana, A.; Buragohaina, Z.; Mondala, M.; Sarmaha, G.; Boraha, G.; Bora, U. Appl. Organometal. Chem. 2014 , 28 , 230{233.
  • 2. Pongracz, P.; Kostas, I. D.; Kollar, L. J. Organomet. Chem. 2013 , 723 , 149{153.
  • 3. Priyaa, S.; Balakrishna, M. S.; Mobin, S. M.; McDonald, R. J. Organomet. Chem. 2003 , 688 , 227{235.
  • 4. Dolinsky, M. C. B.; Lin, W. O.; Dias, M. L. J. Mol. Catal. A: Chem. 2006 , 258 , 267{274.
  • 5. Ly, T. Q.; Woollins, J. D. Coord. Chem. Rev. 1998 , 176 , 451{481.
  • 6. Fei, Z.; Dyson, P. J. Coord. Chem. Rev. 2005 , 249 , 2056{2074.
  • 7. Ghisol , A.; Fliedel, C.; Rosa, V.; Monakhov, K. Y.; Braunstein, P. Organometallics 2014 , 33 , 2523{2534.
  • 8. Nakajima, T.; Fukushima, Y.; Tsuji, M.; Hamada, N.; Kure, B.; Tanase, T. Organometallics 2013 , 32 , 7470{7477.
  • 9. Cimarelli, C.; Fratoni, D.; Palmieri, G. Tetrahedron: Asymmetry 2009 , 20 , 2234{2239.
  • 10. Saikia, B.; Boruah, P. R.; Ali, A. A.; Sarma, D. Tetrahedron Lett . 2015 , 6 , 633{635
  • 11. Naik, S.; Kumaravel, M.; Mague, J. T.; Balakrishna, M. S. Dalton Trans . 2014 , 43 , 1082{1095.
  • 12. Gaw, K. G.; Smith, M. B.; Wright, J. B.; Slawin, A. M. Z.; Coles, S. J.; Hursthouse, M. B.; Tizzard, G. J. J. Organomet. Chem. 2012 , 699 , 39{47.
  • 13. Lamblin, M.; Nassar-Hardy, L.; Hierso, J. C.; Fouquet, E.; Felpin, F. X. Adv. Synth. Catal. 2010 , 352 , 33{79.
  • 14. Bolliger, J. L.; Frech, C. M. Adv. Synth. Catal . 2010 , 352 , 1075{1080.
  • 15. Bolliger, J. L.; Frech, C. M. Chima 2009 , 63 , 23{28.
  • 16. Miyaruna, N.; Suzuki, A. Chem. Rev. 1995 , 95 , 2457{2483.
  • 17. Whitcombe, N. J.; Hii, K. K.; Gibson, S. E. Tetrahedron 2001 , 57 , 7449{7476.
  • 18. Seechurn, C. C. C. J.; Kitching, M. O.; Colacot, T. J.; Snieckus, V. Angew. Chem. Int. Ed . 2012 , 51 , 5062{5085.
  • 19. 9. Fei, Z.; Scopelliti, R.; Dyson, P. J. Dalton Trans. 2003 , 2772{2279.
  • 20. Fei, Z.; Paunescu, E.; Ang, W. H.; Scopelliti, R.; Dyson, P. J. Eur. J. Inorg. Chem. 2014 , 1745{1750.
  • 21. Biricik, N.; Durap, F.; Kayan, C.; Gumgum, B. Heteroatom Chem . 2007 , 18 , 613{616.
  • 22. Biricik, N.; Durap, F.; Gumgum, B; Fei, Z.; Scopelliti, R. Trans. Met. Chem . 2007 , 32 , 877{883.
  • 23. Zhao, D.; Fei, Z.; Ang, W. H. Cent. Eur. J. Chem. 2008 , 6 , 93{98.
  • 24. Biricik, N.; Kayan, C.; Gumgum, B.; Fei, Z.; Scopelliti, R.; Dyson, P. J.; Gurbuz, N.; Ozdemir, I. Inorg. Chim. Acta 2010 , 363 , 1039{1047.
  • 25. Kayan, C.; Biricik, N.; Aydemir, M.; Scopelliti, R. Inorg. Chim. Acta 2012 , 385 , 164{169.
  • 26. Gaw, K. G.; Smith, M. B.; Slawin, A. M. Z. New J. Chem . 2000 , 24 , 429{435.
  • 27. Fei, Z.; Scopellit, R.; Dyson, P. J . Inorg. Chem. 2003 , 42 , 2125{2130.
  • 28. Fei, Z.; Biricik, N.; Scopelliti, R.; Dongbin, Z.; Dyson, P. J. Inorg. Chem. 2004 , 43 , 2228{2230.
  • 29. Priya, S.; Balakrishna, M. S.; Mague, J. T. J. Organomet. Chem. 2003 , 679 , 116{124.
  • 30. Gopalakrishnan, J. Appl. Organomet. Chem. 2009 , 23 , 291{318.
  • 31. Ansell, J.; Wills, M. Chem. Soc. Rev . 2002 , 31 , 259{268.
  • 32. Appleby, T.; Woollins, J. D. Coord. Chem. Rev . 2002 , 235 , 121{140.
  • 33. Bichler, B.; Veiros, L. F.;  Oztopcu, O.; Puchberger, M.; Mereiter, K.; Matsubara, K.; Kirchner, K. A. Organometallics 2011 , 30 , 5928{5942.
  • 34. Rodriguez, M.; Zubiri, I.; Woollins, J. D. Comment. Inorg. Chem. 2003 , 24 , 189{252.
  • 35. Ly, T. Q.; Woollins, J. D. Coord. Chem. Rev : 1998 , 176 , 451{481.
  • 36. Miyaura, N.; Suzuki, A. Chem. Rev . 1995 , 95 , 2457{2483.
  • 37. Johnson, B. F. G. Top. Catal. 2003 , 24 , 147{159.
  • 38. Suzuki, A. J. Organomet. Chem . 1999 , 57 , 147{168.
  • 39. Kotha, S.; Lahiri, K.; Kashninath, D. Tetrahedron Lett. 2002 , 9633{9695.
  • 40. Migowski, P.; Dupont, J. Chem. Eur. J. 2006 , 13 , 32{39.
  • 41. Fei, Z.; Geldbach, T. J.; Zhao, D.; Dyson, P. J. Chem. Eur. J. 2006 , 12 , 2122{2130.
  • 42. Gumgum, B.; Biricik, N.; Durap , F.;  Ozdemir, I.; Gurbuz, N.; Ang, W. H.; Dyson, P. J. Appl. Organometal. Chem . 2007 , 21 , 711{715.
  • 43. Biricik, N.; Durap, F.; Kayan, C.; Gumgum, B.; Gurbuz, N.;  Ozdemir, I.; Ang, W. H.; Fei, Z.; Scopelliti, R. J. Organomet. Chem. 2008 , 693 , 2693{2699.
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: 6
  • Yayıncı: TÜBİTAK
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