Chemistry / Kimya

Permanent URI for this collectionhttps://hdl.handle.net/11147/4072

Browse

Filters

Settings

Has files: YesInstitution Author: search.filters.institutionAuthor.Artok, Levent

Search Results

Now showing 1 - 10 of 28
  • Research Project
    Alkenil Oksiranların Organoborlar ile Paladyum Katalizli Tepkimeleri: 4-aril Ya Da 4-alkenil Sübstitüye Allil Alkollerin Sentezinde Regio ve Stereo Seçimli Bir Yöntem
    (2016) Artok, Levent
    Bu proje kapsamında laboratuvarda sentezlenen alkenil epoksitlerin organoborlar ile rodyum ve paladyum katalizli tepkimeleri gerçekleştirilmiştir. Paladyum katalizli tepkimeler yüksek regio-seçimlilikte gerçekleşerek başlıca 1,4 katılma ürünü olan arillenmiş ya da alkenillenmiş allil alkol (3) türevlerini oluşturmuştur. 1,2 Katılma ürünü olan homoallil alkol (4) türevleri ise genellikle düşük miktarlarda oluşan yan ürünlerdir. Her iki regio-izomer tipi kolon kromatografisi ile ayrılabilmektedir. Ayrıca tepkimeler yüksek stereo-seçimlilik göstermiştir. Genellikle ürünlerin diastereomerik oranı >20:1 olarak saptanmıştır. Epoksit uç karbonunun serbest ve korunmasız bir karbinol grubunun bulunmasının tepkime regio-seçimliliği için gerekli olduğu saptanmıştır. Ayrıca literatürde nadir olarak uygulama alanı olan trifenil arsin ligandının yöntemin regio ve stereo seçimliliğinde fosfin ligandlarına kıyasla çok daha etkin olduğu saptanmıştır. Bununla birlikte rodyum katalizörü ile de yüksek seçimlilikte arzu edilen ürün elde edilse de tepkime verimliliği yeterli bir mertebeye ulaşamamıştır.
  • Article
    Citation - WoS: 1
    Citation - Scopus: 1
    Rhodium(i)-Catalyzed Co-Gas Arylative Dual-Carbonylation of Alkynes With Arylboronic Acids Via the Formyl C-H Activation of Formaldehyde
    (Georg Thieme Verlag, 2021) Morimoto, Tsumoru; Wang, Chuang; Tanimoto, Hiroki; Artok, Levent; Kakiuchi, Kiyomi
    The rhodium(I)-catalyzed reaction of alkynes with aryl-boronic acids in the presence of formaldehyde results in a CO-gas-free arylative dual-carbonylation to produce gamma-butenolide derivatives. The simultaneous loading of phosphine-ligated and phosphine-free rhodium(I) complexes is required for efficient catalysis. The former complex catalyzes the abstraction of a carbonyl moiety from formaldehyde through the activation of its formyl C-H bond (decarbonylation) and the latter catalyzes the subsequent dual-incorporation of the resulting carbonyl unit (carbonylation). The use of larger amounts of the phosphine-ligated rhodium(I) complex generates more carbonyl units, leading to the formation gamma-butenolides via the dual-incorporation of the carbonyl unit.
  • Article
    Citation - WoS: 2
    Citation - Scopus: 2
    Palladium-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, Levent
    Palladium-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: 6
    Citation - Scopus: 6
    Palladium-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, Levent
    A 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: 6
    Citation - Scopus: 6
    Palladium-Catalyzed Coupling of 2-En Carbonates With Terminal Alkynes
    (Elsevier Ltd., 2018) Taç, Doğan; Artok, Levent
    The first palladium-catalysed coupling of the carbonates of (E)-configured conjugated enynols with terminal alkynes is described. This method allows the synthesis of vinyl-allenynes with good yields. It has been determined that the method is not suitable for the (Z)-configured substrates.
  • Article
    Citation - WoS: 13
    Citation - Scopus: 14
    Rhodium(i)-Catalyzed Carbonylative Arylation of Alkynes With Arylboronic Acids Using Formaldehyde as a Carbonyl Source
    (Georg Thieme Verlag, 2014) Wang, Chuang; Morimoto, Tsumoru; Kanashiro, Hiroyuki; Tanimoto, Hiroki; Nishiyama, Yasuhiro; Kakiuchi, Kiyomi; Artok, Levent
    The rhodium(I)-catalyzed reaction of alkynes with arylboronic acids in the presence of formaldehyde resulted in a carbon monoxide gas-free carbonylative arylation to yield α,β-enones. The simultaneous loading of phosphine-ligated and phosphine-free rhodium(I) complexes is required for efficient catalysis, which catalyze the abstraction of a carbonyl moiety from formaldehyde (decarbonylation) and its subsequent introduction into the substrate (carbonylation), respectively.
  • Article
    Citation - WoS: 9
    Citation - Scopus: 10
    Iron-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, Levent
    Acetate 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: 21
    Citation - Scopus: 21
    Palladium-Catalyzed Alkoxycarbonylation of Conjugated Enyne Oxiranes: a Diastereoselective Method for the Synthesis of 7-Hydroxy
    (American Chemical Society, 2015) Kuş, Melih; Artok, Levent; Aygün, Muhittin
    Palladium-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.
  • Article
    Citation - WoS: 21
    Citation - Scopus: 21
    Regio- 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, Levent
    Palladium-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: 7
    Citation - Scopus: 7
    Rhodium-Catalysed Alkoxycarbonylative Cyclisation Reactions of 1,6-Enynes
    (John Wiley and Sons Inc., 2011) Ziyanak, Fırat; Kuş, Melih; Artok, Levent
    The rhodium-catalysed carbonylation of 1,6-enynes possessing an electron-deficient alkenyl moiety in an alcohol reagent in the presence of a rhodium complex proceeded stereo- and chemoselectively to afford exocyclic α,β-enoates.