Imine containing C2-Symmetric chiral half sandwich η6-p-cymene-Ru(II)- phosphinite complexes: Investigation of their catalytic activity in the asymmetric transfer hydrogenation of ketones
作者： Najmuldain Abdullah Saleh , Salih Paşa , Cezmi Kayan , Nermin Meriç , Murat Sünkür
DOI: 10.1016/J.MOLSTRUC.2019.127146
关键词:
摘要: Abstract New chiral C2-symmetric bis(phosphinite) ligands containing imine group were synthesized from 1-({[(1R,2R)-2-{[(2-hydroxynaphthalen-1-yl)methylidene] amino}cyclohexyl]- imino}methyl)- naphthalen-2-ol and two equivalents of Ph2PCl, (i-Pr)2PCl or (Cy)2PCl, in high yields. Binuclear half sandwich η6-p-cymene-Ru(II) complexes the phosphinite by treating [Ru(η6-p-cymene)(μ-Cl)Cl]2 with phosphinites 1:1 M ratio CH2Cl2. Their catalytic activities asymmetric transfer hydrogenation (ATH) investigated for reaction acetophenone derivatives isopropyl alcohol. The corresponding optically active secondary alcohols obtained excellent levels conversion (96–99%) moderate enantioselectivity (up to 60% ee). Among three investigated, complex 4 was most efficient one.
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sci-hub.se 参考文章(36)
Bünyamin Ak, Murat Aydemir, Feyyaz Durap, Nermin Meriç, Akın Baysal, The first application of C2-symmetric ferrocenyl phosphinite ligands for rhodium-catalyzed asymmetric transfer hydrogenation of various ketones Inorganica Chimica Acta. ,vol. 438, pp. 42- 51 ,(2015) , 10.1016/J.ICA.2015.09.003
Bünyamin Ak, Murat Aydemir, Feyyaz Durap, Nermin Meriç, Duygu Elma, Akın Baysal, Highly efficient iridium catalysts based on C2-symmetric ferrocenyl phosphinite ligands for asymmetric transfer hydrogenations of aromatic ketones Tetrahedron-asymmetry. ,vol. 26, pp. 1307- 1313 ,(2015) , 10.1016/J.TETASY.2015.10.002
Nermin Biricik, Feyyaz Durap, Bahattin Gümgüm, Zhaofu Fei, Rosario Scopelliti, Synthesis and reactivity of N,N-bis(diphenylphosphino)dimethylaniline compounds Transition Metal Chemistry. ,vol. 32, pp. 877- 883 ,(2007) , 10.1007/S11243-007-0231-5
Abdelaziz Nait Ajjou, Jean-Louis Pinet, The biphasic transfer hydrogenation of aldehydes and ketones with isopropanol catalyzed by water-soluble rhodium complexes Journal of Molecular Catalysis A: Chemical. ,vol. 214, pp. 203- 206 ,(2004) , 10.1016/J.MOLCATA.2004.01.004
Serkan Dayan, Nilgun Kalaycioglu Ozpozan, Namık Özdemir, Osman Dayan, Synthesis of some ruthenium(II)–Schiff base complexes bearing sulfonamide fragment: New catalysts for transfer hydrogenation of ketones Journal of Organometallic Chemistry. ,vol. 770, pp. 21- 28 ,(2014) , 10.1016/J.JORGANCHEM.2014.08.002
Xiaowei Zhou, Xiaofeng Wu, Bolun Yang, Jianliang Xiao, Varying the ratio of formic acid to triethylamine impacts on asymmetric transfer hydrogenation of ketones Journal of Molecular Catalysis A-chemical. ,vol. 357, pp. 133- 140 ,(2012) , 10.1016/J.MOLCATA.2012.02.002
Murat Aydemir, Khadichakhan Rafikova, Nurzhamal Kystaubayeva, Salih Paşa, Nermin Meriç, Yusuf Selim Ocak, Alexey Zazybin, Hamdi Temel, Nevin Gürbüz, Ismail Özdemir, Ionic liquid based Ru(II)–phosphinite compounds and their catalytic use in transfer hydrogenation: X-ray structure of an ionic compound 1-chloro-3-(3-methylimidazolidin-1-yl)propan-2-ol Polyhedron. ,vol. 81, pp. 245- 255 ,(2014) , 10.1016/J.POLY.2014.05.079
Bünyamin Ak, Murat Aydemir, Yusuf Selim Ocak, Feyyaz Durap, Cezmi Kayan, Akin Baysal, Hamdi Temel, Readily available ferrocenyl-phosphinite ligands for Ru(II)-catalyzed enantioselective transfer hydrogenation of ketones and fabrication of hybrid heterojunctions Inorganica Chimica Acta. ,vol. 409, pp. 244- 253 ,(2014) , 10.1016/J.ICA.2013.09.037
K Ambroziak, Z Rozwadowski, T Dziembowska, B Bieg, Synthesis and spectroscopic study of Schiff bases derived from trans-1,2-diaminocyclohexane. Deuterium isotope effect on 13C chemical shift Journal of Molecular Structure. ,vol. 615, pp. 109- 120 ,(2002) , 10.1016/S0022-2860(02)00213-2
Murat Aydemir, Nermin Meric, Akin Baysal, Yilmaz Turgut, Cezmi Kayan, Sevil Şeker, Mahmut Toğrul, Bahattin Gümgüm, Asymmetric transfer hydrogenation of acetophenone derivatives with novel chiral phosphinite based η6-p-cymene/ruthenium(II) catalysts Journal of Organometallic Chemistry. ,vol. 696, pp. 1541- 1546 ,(2011) , 10.1016/J.JORGANCHEM.2010.12.027