Kuş, Melih
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Kus, M.
Kus, Melih
Kuş, M.
Kuş, M
Kus, M
Kus, Melih
Kuş, M.
Kuş, M
Kus, M
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04.01. Department of Chemistry
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Former Staff
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Documents
11
Citations
150
h-index
7
Documents
0
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0
Scholarly Output
14
Articles
12
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12626/7025
Supervised MSc Theses
1
Supervised PhD Theses
1
WoS Citation Count
170
Scopus Citation Count
166
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0
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1
WoS Citations per Publication
12.14
Scopus Citations per Publication
11.86
Open Access Source
13
Supervised Theses
2
| Journal | Count |
|---|---|
| Journal of Organic Chemistry | 3 |
| Tetrahedron | 2 |
| Organic and Biomolecular Chemistry | 2 |
| Asian Journal of Organic Chemistry | 1 |
| Advanced Synthesis and Catalysis | 1 |
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Article Citation - WoS: 21Citation - Scopus: 21Regio- and Stereoselective Synthesis of 2,3,5-Trienoates by Palladium-Catalyzed Alkoxycarbonylation of Conjugated Enyne Carbonates(American Chemical Society, 2014) Karagöz, Ezgi Şule; Kuş, Melih; Akpınar, Gürkan Eray; Artok, LeventPalladium-catalyzed carbonylation of 2,4-enyne carbonates in an alcohol and under balloon pressure of CO proceeds through 1,5-substitution to yield (E)-2,3,5-trienoates. The olefin geometry of the substrate is important to control the overall stereochemistry of this alkoxycarbonylation method. The reaction proceeds through successive formation of π-allylpalladium with an R3 group oriented syn and σ-allenyl palladium complexes.Article Citation - WoS: 11Citation - Scopus: 2Synthesis of Α,β-Unsaturated Ketones by Rhodium-Catalyzed Carbonylative Arylation of Internal Alkynes With Arylboronic Acids(Georg Thieme Verlag, 2008) Kuş, Melih; Aksın Artok, Özge; Ziyanak, Fırat; Artok, LeventThe Rh-catalyzed reaction of arylboronic acids with internal alkynes under a CO atmosphere in the presence of an acid additive afforded α,β-unsaturated ketones as the major products. Hydroacylation of internal alkynes, except in the case of diaryl acetylenes, proceeded in syn fashion, yielding the E-configured isomer. A mixture of E- and Z-isomers was obtained with diphenyl acetylene. Reactions were also highly regioselective for various nonsymmetric alkynes.Article Iron-Promoted 1,5-Substitution Reaction of Endocyclic Enyne Oxiranes With Memgbr: a Stereoselective Method for the Synthesis of Exocyclic 2,4,5-Trienol Derivatives(MDPI, 2023) Kuş, Melih; Omur, Cenk; Karaca, Sila; Artok, LeventThe iron-promoted 1,5-substitution reaction of endocyclic oxiranes with MeMgBr yields exocyclic 2,4,5-trienols with high diastereomeric ratios of up to 100:0. However, for the method's success, the oxirane ring must have a trans-configuration. The reactions exhibit strong stereoselectivity concerning the methylation mode and the configuration of the resulting exocyclic double bond. Enantiomerically pure enyne oxiranes can be synthesized through Sharpless asymmetric dihydroxylation and subsequent manipulations. With these reagents, it has been possible to produce exocyclic 2,4,5-trienols in enantiopure forms. Importantly, this process maintains chirality without degradation during the center-to-axis transfer of chirality.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, Leventα,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.Article Citation - WoS: 2Citation - Scopus: 2Palladium-Catalysed Regio- and Stereoselective Arylative Substitution of Gamma,delta-Epoxy Esters and Amides by Sodium Tetraaryl Borates(Royal Society of Chemistry, 2020) Bilgi, Yasemin; Kuş, Melih; Artok, LeventPalladium-catalysed reactions of gamma,delta-epoxy-alpha,beta-unsaturated esters and amides with NaBAr(4)reagents proceeded regio- and stereoselectively, producing allylic homoallyl alcohols with aryl-substituents in the allylic position for a wide range of substrates. AsPh(3)was found to be a competent ligand for the arylation reaction, whereas phosphine ligand/Lewis acidic organoboron combinations favoured the substitution reaction by oxygen nucleophiles (e.g.H2O, ROH).Article Citation - WoS: 27Citation - Scopus: 30Rhodium Catalyzed Reaction of Internal Alkynes With Organoborons Under Co Atmosphere: a Product Tunable Reaction(Elsevier Ltd., 2009) Artok, Levent; Kuş, Melih; Aksın, Özge; Dege, Fatma Nurcan; Özkılınç, Fatma YeldaAlkynes react with organoborons under a CO atmosphere in the presence of a rhodium(I) catalyst to afford mainly 5-aryl-2(5H)-furanones, α,β-unsaturated ketones, and indanones. The product selectivity can be tuned by modifying the reaction conditions.Article Citation - WoS: 6Citation - Scopus: 6Palladium-Catalysed Reactions of Conjugated Enyne Oxiranes With Organoborons: a Diastereoselective Method of the Synthesis of 2,4,5-Trienol Derivatives(Elsevier, 2017) Ziyanak, Fırat; Kuş, Melih; Alkan Karadeniz, Leman; Artok, LeventA palladium-catalysed reaction of conjugated enyne oxiranes with organoboron reagents is described. This method allows aryl-substituted vinylallenes containing a hydroxyl group on the allylic position to be synthesized, with good diastereomeric ratios, under mild conditions.Article Citation - WoS: 37Citation - Scopus: 38Palladium-Catalyzed Alkoxycarbonylation of (z)-2 Carbonates Leading To 2,3,5-Trienoates(American Chemical Society, 2011) Akpınar, G. Eray; Kuş, Melih; Üçüncü, Muhammed; Karakuş, Erman; Artok, LeventPd(0)-catalyzed carbonylation of (Z)-2-en-4-yn carbonates in the presence of a balloon pressure of CO in an alcohol donates vinylallenyl esters with an exclusively E-configuration and in high yields. The fact that no such reactivity could be observed with E-configured enyne carbonates may indicate that the reaction is promoted via the cooperative coordination of palladium with both alkynyl and carbonate moieties.Article Citation - WoS: 9Citation - Scopus: 10Iron-Promoted 1,5-Substitution (sn2' Reactions of Enyne Acetates and Oxiranes With Grignard Reagents(Wiley, 2017) Taç, Doğan; Aytaç, İsmet Arınç; Karatavuk, Ali Osman; Kuş, Melih; Ziyanak, Fırat; Artok, LeventAcetate derivatives of 2-en-4-yne alcohols 1 and enyne oxiranes 4 regioselectively underwent 1,5-substitution (SN2′′) reactions with Grignard reagents in the presence of an iron compound to provide vinylallenes exclusively with the (E)-configuration. An alkali salt was needed to avoid the hydride-promoted reductive 1,5-substitution pathway for 1, whereas no such additive was needed for the effective conversion of 4 into the desired alkylated or arylated vinylallene structure.Article Citation - WoS: 21Citation - Scopus: 21Palladium-Catalyzed Alkoxycarbonylation of Conjugated Enyne Oxiranes: a Diastereoselective Method for the Synthesis of 7-Hydroxy(American Chemical Society, 2015) Kuş, Melih; Artok, Levent; Aygün, MuhittinPalladium-catalyzed alkoxycarbonylative 1,5-substitution of conjugated enyne oxiranes provides a diastereoselective route to (E)-configured 7-hydroxy-2,3,5-trienoates. The reactions proceeded in a highly stereoselective manner, possibly through sequential formation of π-allylpalladium and σ-vinylallenyl palladium complexes. The major diastereomeric form of the product is determined by the configuration of the alkenyl moiety of the substrate.