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Journals / Turkish Journal of Chemistry / 2015 / Cilt: 39 - Sayı: 6

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

Nermin BİRİCİK
Nermin MERİÇ
Cezmi KAYAN
Zeynep ÖZGEN
Sevil Şeker AZİZOĞLU
Bahattin GÜMGÜM
Pages
1257–1264
Publication Date
2015-12-04
DOI
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AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

Compounds \textbf{4b} and \textbf{4c }were proved to be excellent catalysts for Suzuki and Heck cross-coupling reactions.

📌 3 Key Takeaways

🎯
Objective & Hypothesis:A series of new aminophosphines [Ph$_{2}$PHN-C$_{6}$H$_{4}$-R, where R = $o$-SH (\textbf{4a}), $m$-SH (\textbf{4b) or }$p$-SH (\textbf{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.
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Key Findings & Data:The new compounds were characterized by NMR and IR spectroscopy and microanalysis.
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Conclusion & Impact:Compounds \textbf{4b} and \textbf{4c }were proved to be excellent catalysts for Suzuki and Heck cross-coupling reactions.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Aminophosphine · synthesis · catalysis

Abstract

A series of new aminophosphines [Ph$_{2}$PHN-C$_{6}$H$_{4}$-R, where R = $o$-SH (\textbf{4a}), $m$-SH (\textbf{4b) or }$p$-SH (\textbf{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 \textbf{4b} and \textbf{4c }were proved to be excellent catalysts for Suzuki and Heck cross-coupling reactions.

Özet

A series of new aminophosphines [Ph$_{2}$PHN-C$_{6}$H$_{4}$-R, where R = $o$-SH (\textbf{4a}), $m$-SH (\textbf{4b) or }$p$-SH (\textbf{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 \textbf{4b} and \textbf{4c }were proved to be excellent catalysts for Suzuki and Heck cross-coupling reactions.

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Cite This Article

BİRİCİK, N., MERİÇ, N., KAYAN, C., ÖZGEN, Z., AZİZOĞLU, S. Ş., GÜMGÜM, B. (2015). Synthesis of new thiol-derivatized aminophosphines and their catalytic activities in C--C coupling reactions. Turkish Journal of Chemistry, Cilt: 39 - Sayı: 6, 1257–1264. https://ajindex.com/articles/184612

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References (23)

  1. of NHPPh2), 134.78 (C4-Ar), 134.73 (C2-Ar), 132.77 (d, J = 21.1 Hz, o -carbons of NHPPh2), 129.16 (s, p - carbons of NHPPh2), 128.50 (d, J = 6.0 Hz, m -carbons of NHPPh2), 115.68 (C3-Ar); assignment was based on the1H–13C HETCOR and1H–1H COSY spectra;31P{1H} NMR (CDCl3, ppm): δ 36.71 (s). IR (KBr pellet in cm −1 ).epsυ 3278 (N–H) 3147, 3016 (aromatic C–H), 2532 (S–H), 1431 (P–Ph), 738 (P–NH); C18H16NSP Pongr´acz, P.; Kostas, I. D.; Koll´ar, L. J. Organomet. Chem. 2013, 723, 149–153.
  2. Priyaa, S.; Balakrishna, M. S.; Mobin, S. M.; McDonald, R. J. Organomet. Chem. 2003, 688, 227–235.
  3. Dolinsky, M. C. B.; Lin, W. O.; Dias, M. L. J. Mol. Catal. A: Chem. 2006, 258, 267–274.
  4. Ly, T. Q.; Woollins, J. D. Coord. Chem. Rev. 1998, 176, 451–481.
  5. Fei, Z.; Dyson, P. J. Coord. Chem. Rev. 2005, 249, 2056–2074.
  6. Ghisolfi, A.; Fliedel, C.; Rosa, V.; Monakhov, K. Y.; Braunstein, P. Organometallics 2014, 33, 2523–2534.
  7. Nakajima, T.; Fukushima, Y.; Tsuji, M.; Hamada, N.; Kure, B.; Tanase, T. Organometallics 2013, 32, 7470–7477.
  8. Cimarelli, C.; Fratoni, D.; Palmieri, G. Tetrahedron: Asymmetry 2009, 20, 2234–2239.
  9. Saikia, B.; Boruah, P. R.; Ali, A. A.; Sarma, D. Tetrahedron Lett. 2015, 6, 633–635
  10. Naik, S.; Kumaravel, M.; Mague, J. T.; Balakrishna, M. S. Dalton Trans. 2014, 43, 1082–1095.
  11. 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.
  12. Lamblin, M.; Nassar-Hardy, L.; Hierso, J. C.; Fouquet, E.; Felpin, F. X. Adv. Synth. Catal. 2010, 352, 33–79.
  13. Bolliger, J. L.; Frech, C. M. Adv. Synth. Catal. 2010, 352, 1075–1080.
  14. Bolliger, J. L.; Frech, C. M. Chima 2009, 63, 23–28.
  15. Miyaruna, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457–2483.
  16. Whitcombe, N. J.; Hii, K. K.; Gibson, S. E. Tetrahedron 2001, 57, 7449–7476.
  17. Seechurn, C. C. C. J.; Kitching, M. O.; Colacot, T. J.; Snieckus, V. Angew. Chem. Int. Ed. 2012, 51, 5062–5085. 9. Fei, Z.; Scopelliti, R.; Dyson, P. J. Dalton Trans. 2003, 2772–2279.
  18. Fei, Z.; P˘aunescu, E.; Ang, W. H.; Scopelliti, R.; Dyson, P. J. Eur. J. Inorg. Chem. 2014, 1745–1750.
  19. Biricik, N.; Durap, F.; Kayan, C.; G¨umg¨um, B. Heteroatom Chem. 2007, 18, 613–616.
  20. Biricik, N.; Durap, F.; Gumgum, B; Fei, Z.; Scopelliti, R. Trans. Met. Chem. 2007, 32, 877–883.
  21. Zhao, D.; Fei, Z.; Ang, W. H. Cent. Eur. J. Chem. 2008, 6, 93–98.
  22. Biricik, N.; Kayan, C.; G¨umg¨um, B.; Fei, Z.; Scopelliti, R.; Dyson, P. J.; Gurbuz, N.; Ozdemir, I. Inorg. Chim. Acta 2010, 363, 1039–1047.
  23. Kayan, C.; Biricik, N.; Aydem