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Asymmetric Transfer Hydrogenation of Aromatic Ketones Catalyzed by New Chiral C2-Symmetric Bis(sulfonyl) tetraaza Ligands Complexed with [Ru(η 6-p-cymene)Cl2]2 in Water

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Abstract

In this report, a new series of C2-symmetric bis(sulfonyl) tetraaza ligands were synthesized from (1S,2S)-1,2-diarylethylenediamine analogues and tested in the asymmetric transfer hydrogenation (ATH) of aromatic ketones by complexing with [Ru(η 6-p-cymene)Cl2]2 employing sodium formate as hydrogen source in neat water. A moderate to excellent conversion (~99.8 %) and overall satisfying enantioselectivity (~92.8 %) were obtained with varied electronic and steric effects of the substituents on ligands and substrates.

Graphical Abstract

A new series of C2-symmetric bis(sulfonyl) tetraaza ligands was synthesized from (1S,2S)-1,2-diarylethylenediamine analogues and tested in the asymmetric transfer hydrogenation of aromatic ketones by complexing with [Ru(η6-p-cymene)Cl2]2 employing formate sodium as hydrogen source in neat water. A moderate to excellent conversion (~99.8 %) and overall satisfying enantioselectivity (~92.8 %) were obtained with varied electronic and steric effects of the substituents on ligands and substrates.

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References

  1. Noyori R, Hashiguchi S (1997) Acc Chem Res 30:97–102

    Article  CAS  Google Scholar 

  2. Noyori R, Yamakawa M, Hashiguchi S (2001) J Org Chem 66:7931–7944

    Article  CAS  Google Scholar 

  3. Yamakawa M, Ito H, Noyori R (2000) J Am Chem Soc 122:1466–1478

    Article  CAS  Google Scholar 

  4. Hashiguchi S, Fujii A, Takehara J, Ikariya T, Noyori R (1995) J Am Chem Soc 117:7562–7563

    Article  CAS  Google Scholar 

  5. Wang C, Wu XF, Xiao JL (2008) Chem Asian J 3:1750–1770

    Article  CAS  Google Scholar 

  6. Hannedouche J, Clarkson GJ, Wills M (2004) J Am Chem Soc 126:986–987

    Article  CAS  Google Scholar 

  7. Cheung FK, Hayes AM, Hannedouche J, Yim ASY, Wills M (2005) J Org Chem 70:3188–3197

    Article  CAS  Google Scholar 

  8. Hayes AM, Morris DJ, Clarkson GJ, Wills M (2005) J Am Chem Soc 127:7318–7319

    Article  CAS  Google Scholar 

  9. Morris DJ, Hayes AM, Wills M (2006) J Org Chem 71:7035–7044

    Article  CAS  Google Scholar 

  10. Cheung FK, Graharn MA, Minissi F, Wills M (2007) Organometallics 26:5346–5351

    Article  CAS  Google Scholar 

  11. Cheung FK, Lin CX, Minissi F, Criville AL, Graharn MA, Fox DJ, Wills M (2007) Org Lett 9:4659–4662

    Article  CAS  Google Scholar 

  12. Cortez NA, Aguirre G, Parra-Hake M, Somanathan R, Arita AJ, Cooksy AL, de Parrodi CA, Huelgas G (2010) Synth Commun 41:73–84

    Google Scholar 

  13. Baratta W, Benedetti F, Zotto AD, Fanfoni L, Felluga F, Magnolia S, Putignano E, Rigo P (2010) Organometallics 29:3563–3570

    Article  CAS  Google Scholar 

  14. Reetz MT, Li X (2006) J Am Chem Soc 128:1044–1045

    Article  CAS  Google Scholar 

  15. Ahlford K, Adolfsson H (2011) Catal Commun 12:1118–1121

    Article  CAS  Google Scholar 

  16. Charles MM, Schwarz I (2000) Tetrahedron Lett 41:8999–9003

    Article  Google Scholar 

  17. Ranocchiari M, Mezzetti A (2009) Organometallics 28:1286–1288

    Article  CAS  Google Scholar 

  18. Sterk D, Stephan MS, Mohar B (2004) Tetrahedron Lett 45:535–537

    Article  CAS  Google Scholar 

  19. Cortez NA, Rodríguez-Apodaca R, Aguirre G, Parra-Hake M, Cole T, Somanathan R (2006) Tetrahedron Lett 47:8515–8518

    Article  CAS  Google Scholar 

  20. Cortez NA, Aguirre G, Parra-Hake M, Somanathan R (2009) Tetrahedron Lett 50:2228–2231

    Article  CAS  Google Scholar 

  21. Montalvo-González R, Chávez D, Aguirre G, Parra-Hake M, Somanathan R (2010) J Braz Chem Soc 21:431–435

    Article  Google Scholar 

  22. Hong YL, Tan HJ, Qiu J, Shen L (2012) Synth React Inorg Met-Org Nano-Met Chem 42:502–506

    Article  CAS  Google Scholar 

  23. Rhyoo HY, Park HJ, Chung YK (2001) Chem Commun 2064–2065

  24. Ma YP, Liu H, Chen L, Cui X, Zhu J, Deng JG (2003) Org Lett 5:2103–2106

    Article  CAS  Google Scholar 

  25. Wu XF, Li XG, Hems W, King F, Xiao JL (2004) Org Biomol Chem 2:1818–1821

    Article  CAS  Google Scholar 

  26. Kim H, Nguyen Y, Yen PHC, Chagal L, Lough AJ, Kim BM, Chin J (2008) J Am Chem Soc 130:12184–12191

    Article  CAS  Google Scholar 

  27. Kim H, Staikova M, Lough AJ, Chin J (2009) Org Lett 11:157–160

    Article  CAS  Google Scholar 

  28. Lee DN, Kim H, Mui L, Myung SW, Chin J, Kim HJ (2009) J Org Chem 74:3330–3334

    Article  CAS  Google Scholar 

  29. Cartigny D, Puntener K, Ayad T, Scalone M, Ratovelomanana-Vidal V (2010) Org Lett 12:3788–3791

    Article  CAS  Google Scholar 

  30. Tang YF, Xiang J, Cun LF, Wang YQ, Zhu J, Liao J, Deng JG (2010) Tetrahedron Asymmetry 21:1900–1905

    Article  CAS  Google Scholar 

  31. Wang L, Zhou Q, Qu C, Wang QW, Cun LF, Zhu J, Deng JG (2013) Tetrahedron 69:6500–6506

    Article  CAS  Google Scholar 

  32. Yamakawa M, Ito H, Noyori R (2000) J Am Chem Soc 122:1466–1478

    Article  CAS  Google Scholar 

  33. Soni R, Cheung FK, Clarkson GC, Martins JED, Grahamb MA, Wills M (2011) Org Biomol Chem 9:3290–3294

    Article  CAS  Google Scholar 

  34. Kenny JA, Palmer MJ, Smith ARC, Walsgrove T, Wills M (1999) Synlett 10:1615–1617

    Article  Google Scholar 

  35. Zhao JF, Dou HJ, Zhou YH, Qu JP (2011) Chem J Chin Universities 32:2331–2334

    CAS  Google Scholar 

Download references

Acknowledgments

We express our gratitude to the Public Benefit Project of Zhejiang Science and Technology Department for financial Support through Project No. 2012C21098 and the National Natural Science Foundation of China (21101048).

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Authors and Affiliations

  1. College of Material Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, 310036, People’s Republic of China

    Xungao Liu, Tian Zhang, Yingying Hu & Liang Shen

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  1. Xungao Liu
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  2. Tian Zhang
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  3. Yingying Hu
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  4. Liang Shen
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Correspondence to Liang Shen.

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Liu, X., Zhang, T., Hu, Y. et al. Asymmetric Transfer Hydrogenation of Aromatic Ketones Catalyzed by New Chiral C2-Symmetric Bis(sulfonyl) tetraaza Ligands Complexed with [Ru(η 6-p-cymene)Cl2]2 in Water. Catal Lett 144, 1289–1295 (2014). https://doi.org/10.1007/s10562-014-1254-0

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