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Asymmetric transfer hydrogenation of ketones with Ru(II) and Ir(III) phosphinite complexes

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  1. Tez No: 418833
  2. Yazar: AHMED SABRI
  3. Danışmanlar: DOÇ. DR. MURAT AYDEMİR
  4. Tez Türü: Yüksek Lisans
  5. Konular: Kimya, Chemistry
  6. Anahtar Kelimeler: Belirtilmemiş.
  7. Yıl: 2016
  8. Dil: İngilizce
  9. Üniversite: Dicle Üniversitesi
  10. Enstitü: Fen Bilimleri Enstitüsü
  11. Ana Bilim Dalı: Kimya Ana Bilim Dalı
  12. Bilim Dalı: Belirtilmemiş.
  13. Sayfa Sayısı: 73

Özet

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Özet (Çeviri)

Transition metal catalyzed homogeneous asymmetric catalysis is an important field of research, and the design and development of efficient ligands for this process have been withdrawing considerable interest. Today, a great number of chiral compounds and enantiomerically pure drugs are obtained through these reactions. It is known that the reactivity and stereoselectivity of an asymmetric conversion depend on the structure of the chiral ligand coordinated to the transition metal, thus, the design and synthesis of efficient chiral ligands are important in this field. Furthermore, transfer hydrogenation reactions are simple, environmentally benign and easy to handle and reaction conditions are not so harsh. Since the ferrocene moiety is easily modifiable and has highly electron donating property, it has been widely studied as a backbone of chiral phosphine ligand. In addition, the ferrocene derived ligands generally crystallize readily and they are relatively air stable compared to their nonferrocenyl analogous. These features are beneficial for purification and usage of the ligands. Furthermore, the unique structure of ferrocenes allows one to design a variety of chiral ferrocenyl phosphine ligands, which are useful tools in metal-catalyzed asymmetric reactions. In the present work, six precursors for alcohols were prepared, from which six different alcohols were obtained. Then, six phosphinite ligands, 1-6 were synthesized by the reaction of these compounds with Ph2PCl. Treatment of 1-4 with Ir gave Ir(III) complexes, 1a-4a, while reaction of ligands 5 and 6 with [Ru(η6-p-cymene)Cl2]2 or [Ru(η6-benzene)Cl2]2 afforded new Ru(II) complexes 5a-b and 6a-b, which were characterized by spectroscopic methods, such as NMR and IR, and elemental analysis. Finally, these complexes were employed as catalyst in transfer hydrogenation reaction of ketones. Generally, high conversions and with some complexes enantiomeric excess (ee) up to 98 % were obtained.

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