Please use this identifier to cite or link to this item: https://hdl.handle.net/11147/5705
Title: Metal-catalyzed coupling reactions of conjugated enyne alcohol derivatives with organometallics: An effective method in synthesis of functionalized vinylallenes
Other Titles: Konjuge enin alkol türevlerinin organometalikler ile metal katalizli kenetlenme tepkimeleri: Fonksiyonlanmış vinilallenlerin sentezinde verimli bir yöntem
Authors: Artok, Levent
Taç, Doğan
Keywords: Organic chemistry
Allenes
Alkynylation
Alkylation
Metal catalysts
Organic compounds
Issue Date: Nov-2016
Publisher: Izmir Institute of Technology
Source: Taç, D. (2016). Metal-catalyzed coupling reactions of conjugated enyne alcohol derivatives with organometallics:|bAn effective method in synthesis of functionalized vinylallenes. Unpublished doctoral dissertation, İzmir Institute of Technology, İzmir, Turkey
Abstract: Transformations of organic compounds using transition metals are common methods in the toolbox of a synthetic chemist. Metal catalyzed C-C couplings are one of the most useful technique in this toolbox. Conjugate addition of soft/hard carbon nucleophiles to form allenes which are synthetically and pharmaceutically key precursors has been of great interest. Within the scope of this thesis functionalized vinylallene derivatives were prepared in two different types of new methods. The first method is Pd/Cu-catalyzed conjugate addition of terminal alkynes on enyne carbonates. The other method is iron-catalyzed conjugate addition of Grignard reagents on enyne acetates. In the case of the former method, alkynyl-substituted vinylallenes (1,3,4-trien-6-yne) were prepared with optimized conditions up to 91% yield in relatively short reaction periods. The optimized conditions of the cross coupling were successfully applied with various types of terminal alkynes and enyne substrates. The latter method involves the synthesis of alkylated vinylallenes with up to 90% yield with proper conditions.
Organik bileşiklerin geçiş metalleri kullanılarak dönüşümleri sentetik kimyagerlerin sık olarak kullandığı metodlardandır. Yumuşak veya sert nükleofiller ile sentetik ve potent ilaç etken madde olarak vinilallen türevlerinin oluşturulması en sık kullanılan yöntemlerden biridir ve günümüzde bu yöntemler yüksek ilgi görmektedir. Bu tez çalışmasında fonksiyonlandırılmış vinilallen türevleri iki tip yeni eşleşme tepkimesi ile hazırlanmıştır. İlk metod paladyum/bakır-katalizi ile terminal alkinlerin konjuge katılma ile enin karbonatlara katılma tepkimesidir. İkinci metod ise bakır-katalizli Grignard reaktiflerinin enin asetatlar ile 1,5-(SN’’) sübstitüsyon tepkimeleridir. İlk metod ile alkinil gruplu vinilallen (1,3,4-trien-6-in) bileşiklerin sentezi optimize koşullar altında %91 verime kadar sentezlenebilmiştir. Eşleşme tepkimelerinin optimize koşulları çeşitli terminal alkinenin substratlara başarılı olarak uygulanabilmiştir. İkinci metod ile vinilallen türevleri alkil ve aril Grignard reaktifleri eşliğinde %90 veime kadar sentezlenebilmiştir.
Description: Thesis (Doctoral)--İzmir Institute of Technology, Chemistry, İzmir, 2016
Includes bibliographical references (leaves: 85-90)
Text in English; Abstract: Turkish and English
x, 197 leaves
URI: http://hdl.handle.net/11147/5705
Appears in Collections:Phd Degree / Doktora

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