Master Degree / Yüksek Lisans Tezleri
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Master Thesis Synthesis of Α,β-Unsaturated Ketones by Rhodium-Catalyzed Carbonylative Arylation of Internal Alkynes With Arylboronic Acids(Izmir Institute of Technology, 2009) Kuş, Melih; Artok, Levent; Kuş, Melih; Artok, Levent; 04.01. Department of Chemistry; 04. Faculty of Science; 01. Izmir Institute of Technologyα,β-Unsaturated ketones are important key reagents in organic synthesis. They are commonly synthesised through an aldol condensation reaction.Since Hayashi et al. reported the first Rh-catalyzed addition of aryl- and alkenylboronic acids to α,β-unsaturated ketones, the Rh-catalyzed addition of organoboron reagents to various unsaturated systems has become increasingly popular as a method of constructing C.C bonds. Organoboron reagents readily undergo transmetalation with Rh to form arylrhodium(I) species that are capable of inducing the nucleophilic arylation of various electrophilic sites (Sakai, et al. 1997, Hayashi and Yamasaki 2003). In this work, we have succesfully performed another example of the Rhcatalyzed reaction of arylboronic acids: a reaction of arylboronic acids with alkynes under a CO atmosphere to yield α,β-unsaturated ketones (Kuş, et al. 2008). As a consequence, the methodology established in this study proposes arelatively mild and simple way for the synthesis of α,β-unsaturated ketones.Master Thesis The Syntheses of Indanones and Indenones Via Rhodium Catalyzed Carbonylative Arylation of Alkynes(Izmir Institute of Technology, 2009) Özkılınç, Fatma Yelda; Artok, Levent; Artok, Levent; 04.01. Department of Chemistry; 04. Faculty of Science; 01. Izmir Institute of TechnologyIndanones and indenones are important classes of compounds in organic chemistry. These structural motifs are found in various types of natural compounds and also can be used as intermediates in the synthesis of a variety of molecules.In this study, indanones and indenones were synthesized via rhodium catalyzed reaction of alkynes with arylboroxines under a CO atmosphere. Reactions were performed using para- and meta- substituted phenylboroxines. Higher yields were obtained for indanones with methyl- substitution on para- and meta-positions of phenylboroxines than methoxy-substituted ones. However, by using phenylboroxine with an electron withdrawing group, a lower yield of indanone was observed. Higher yields of indanone were obtained with electron poor diaryl acetylenes than electron rich ones.As a general result, the yields of indanone were higher than the yields of indenones at the end of the reaction. The desired products were purified with silica gel column chromatography and the structure of indanones and indenones were determined using GC, GC-MS, NMR, FT-IR and HRMS techniques.