Ticari olarak temin edilen homojen katalizöretkisinde aril azidlerin primer aminlere indirgenmesi
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Dosyalar
Tarih
2022
Yazarlar
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
Düzce Üniversitesi
Erişim Hakkı
info:eu-repo/semantics/openAccess
Özet
Aminler, boya, beşeri ilaç, reçine, zirai ve haşere ilaç endüstrisinde değerli hammadde kimyasallarının sentezinde önemli bir yere sahiptir. İlaç endüstrisinde serotonin, klorfeniramin, aktinomisin, rifamisin benzeri moleküllerin sentetik olarak eldesi ve geliştirilmesi önemli bir çalışma sahasıdır. Sentetik organik kimyacılar bundan dolayı primer aminlerin sentezine odaklanmışlardır. Çalışmada, aril azidlerden primer aminlerin sentezi için yeni bir yöntem geliştirilmiştir. Bu amaçla ticari olarak temin edilebilen ve homojen bir katalizör olan 2,2'-Bis(difenilfosfin)-1,1'-binaftil]palladyum(II) klorür (BINAP.PdCl2) ve hidrojen kaynağı olarak sodyum borhidrür (NaBH4) kullanılmıştır. BINAP.PdCl2 katalizörü, aril azidlerin hidrojenasyon reaksiyonunda ilk kez kullanılmıştır. Katalizörün ve indirgeyici reaktifin etkisi ile oda şartlarında hidrojenasyon reaksiyonları gerçekleştirilmiştir. Reaksiyonlarda çözücü olarak suyun kullanılması sentetik organik kimya için önemli bir gelişmedir. Çevre dostu bir çözücü içerisinde 7 farklı aril azid türevleri üzerinde denemeler gerçekleştirilerek 15 dakika içerisinde %95'in üzerinde verimlerle primer aminlerin sentezi gerçekleştirilmiştir. Reaksiyonlar ve gerekli izolasyon süreçleri tamamlandıktan sonra 1H ve 13C NMR spektrumları ile primer amin türevlerinin karakterizasyonu gerçekleştirilmiştir.
Amines have an important place in the synthesis of valuable raw material chemicals in the dye, human medicine, resin, agricultural and pesticide industries. Synthetic synthesis and development of serotonin, chlorpheniramine, actinomycin, rifamycin-like molecules is an important field of study in the pharmaceutical industry. Synthetic organic chemists have therefore focused on the synthesis of primary amines. In the study, a new method was developed for the synthesis of primary amines from aryl azides. For this purpose, 2,2'-Bis(diphenylphosphine)-1,1'-binaphthyl]palladium(II) chloride (BINAP.PdCl2), a commercially available homogeneous catalyst, and sodium borohydride (NaBH4) as hydrogen source were used. BINAP.PdCl2 catalyst was used for the first time in the hydrogenation reaction of aryl azides. Hydrogenation reactions were carried out at room conditions with the effect of catalyst and reducing reagent. The use of water as a solvent in the reactions is an important development for synthetic organic chemistry. Experiments were carried out on 7 different aryl azide derivatives in an environmentally friendly solvent, and primary amines were synthesized in 15 minutes with yields over 95%. After the reactions and necessary isolation processes were completed, the characterization of the primary amine derivatives was carried out with 1H and 13C NMR spectra.
Amines have an important place in the synthesis of valuable raw material chemicals in the dye, human medicine, resin, agricultural and pesticide industries. Synthetic synthesis and development of serotonin, chlorpheniramine, actinomycin, rifamycin-like molecules is an important field of study in the pharmaceutical industry. Synthetic organic chemists have therefore focused on the synthesis of primary amines. In the study, a new method was developed for the synthesis of primary amines from aryl azides. For this purpose, 2,2'-Bis(diphenylphosphine)-1,1'-binaphthyl]palladium(II) chloride (BINAP.PdCl2), a commercially available homogeneous catalyst, and sodium borohydride (NaBH4) as hydrogen source were used. BINAP.PdCl2 catalyst was used for the first time in the hydrogenation reaction of aryl azides. Hydrogenation reactions were carried out at room conditions with the effect of catalyst and reducing reagent. The use of water as a solvent in the reactions is an important development for synthetic organic chemistry. Experiments were carried out on 7 different aryl azide derivatives in an environmentally friendly solvent, and primary amines were synthesized in 15 minutes with yields over 95%. After the reactions and necessary isolation processes were completed, the characterization of the primary amine derivatives was carried out with 1H and 13C NMR spectra.
Açıklama
Anahtar Kelimeler
Kimya, Chemistry
