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Metal-Catalyzed Coupling Reactions of Conjugated Enyne Alcohol Derivatives With Organometallics: an Effective Method in Synthesis of Functionalized Vinylallenes
(Izmir Institute of Technology, 2016) Taç, Doğan; Artok, Levent; Artok, Levent; 04.01. Department of Chemistry; 04. Faculty of Science; 01. Izmir Institute of Technology
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.

Phd Degree / Doktora