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  • 1.
    Carrasco, Sergio
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Sanz-Marco, Amparo
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Martin-Matute, Belén
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Fast and Robust Synthesis of Metalated PCN-222 and Their Catalytic Performance in Cycloaddition Reactions with CO22019Ingår i: Organometallics, ISSN 0276-7333, E-ISSN 1520-6041, Vol. 38, nr 18, s. 3429-3435Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    A simple and quick setup for the synthesis of PCN-222 and of a variety of metalated PCN-222(Co, Ni, Cu, and Zn), using of a microwave reactor, is reported for CO2 fixation. Metalation of prophyrins by microwave heating has been evaluated through UV-vis titration. PCN-222(M) were obtained in a three-step, one-pot reaction in a remarkable 72% yield in only 30 min. The materials have been characterized using a variety of techniques. A study of CO2 fixation through cycloaddition with epoxides and azidirines using metalated PCNs as catalysts is described. Cyclic carbonates and oxazolidinones were formed using CO2 at atmospheric pressure under mild conditions. Higher activity was observed when PCN-222(Co) was used compared to that with PCN-222(Ni, Cu, Zn).

  • 2.
    Erbing, Elis
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Sanz-Marco, Amparo
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Vazquez-Romero, Ana
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Malmberg, Jesper
    Johansson, Magnus J.
    Gomez-Bengoa, Enrique
    Martín-Matute, Belén
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Base- and Additive-Free Ir-Catalyzed ortho-Iodination of Benzoic Acids: Scope and Mechanistic Investigations2018Ingår i: ACS Catalysis, ISSN 2155-5435, E-ISSN 2155-5435, Vol. 8, nr 2, s. 920-925Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    A protocol for the C-H activation/iodination of benzoic acids catalyzed by a simple iridium complex has been developed. The method described in this paper allows the ortho-selective iodination of a variety of benzoic acids under extraordinarily mild conditions in the absence of any additive or base in 1,1,1,3,3,3-hexafluoroisopropanol as the solvent. The iridium catalyst used tolerates air and moisture, and selectively gives ortho-iodobenzoic acids with high conversions. Mechanistic investigations revealed that an Ir(III)/Ir(V) catalytic cycle operates, and that the unique properties of HFIP enables the C-H iodination using the carboxylic moiety as a directing group.

  • 3.
    Martinez-Erro, Samuel
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    García-Vázquez, Víctor
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Sanz-Marco, Amparo
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Martín-Matute, Belén
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Selective Synthesis and Stereospecific Isomerization of Chiral Allylic HalidesManuskript (preprint) (Övrigt vetenskapligt)
  • 4.
    Martinez-Erro, Samuel
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Sanz-Marco, Amparo
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Bermejo Gómez, Antonio
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Vazquez-Romero, Ana
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Ahlquist, Mårten S. G.
    Martín-Matute, Belén
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Base-Catalyzed Stereospecific Isomerization of Electron-Deficient Allylic Alcohols and Ethers through Ion-Pairing2016Ingår i: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 138, nr 40, s. 13408-13414Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    A mild base-catalyzed strategy for the isomerization of allylic alcohols and allylic ethers has been developed. Experimental and computational investigations indicate that transition metal catalysts are not required when basic additives are present. As in the case of using transition metals under basic conditions, the isomerization catalyzed solely by base also follows a stereospecific pathway. The reaction is initiated by a rate-limiting deprotonation. Formation of an intimate ion pair between an allylic anion and the conjugate acid of the base results in efficient transfer of chirality. Through this mechanism, stereochemical information contained in the allylic alcohols is transferred to the ketone products. The stereospecific isomerization is also applicable for the first time to allylic ethers, yielding synthetically valuable enantioenriched (up to 97% ee) enol ethers.

  • 5.
    Molleti, Nagaraju
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Martinez-Erro, Samuel
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Carretero Cerdán, Alba
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi. Universidad País Vasco, Spain.
    Sanz-Marco, Amparo
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Gomez-Bengoa, Enrique
    Martín-Matute, Belén
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Base-Catalyzed [1,n]-Proton Shifts in Conjugated Polyenyl Alcohols and Ethers2019Ingår i: ACS Catalysis, ISSN 2155-5435, E-ISSN 2155-5435, Vol. 9, nr 10, s. 9134-9139Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    The isomerization of dienyl alcohols and polyenyl alkyl ethers catalyzed by TBD (1,5,7-triazabicyclo[4.4.0]dec-5-ene) under metal-free conditions is presented. Two reaction pathways have been observed. For dienyl alcohols, the reaction proceeds by a [1,3]-proton shift to give γ,δ-unsaturated ketones exclusively. On the other hand, the reaction with polyenyl alkyl ethers gives the corresponding conjugated vinyl ethers in good yields (up to 85%), with regioselectivities up to >20:1. Experimental and computational investigations suggest that the mechanism proceeds through consecutive “chain-walking” proton shifts (“base walk”) mediated by TBD.

  • 6.
    Sanz-Marco, Amparo
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Martinez-Erro, Samuel
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Martín-Matute, Belén
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Selective Synthesis of Unsymmetrical Aliphatic Acyloins through Oxidation of Iridium Enolates2018Ingår i: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 24, nr 45, s. 11564-11567Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    The first method to access unsymmetrical aliphatic acyloins is presented. The method relies on a fast 1,3-hydride shift mediated by an Ir-III complex in allylic alcohols followed by oxidation with TEMPO+. The direct conversion of allylic alcohols into acyloins is achieved in a one-pot procedure. Further functionalization of the C alpha' of the alpha-amino-oxylated ketone products gives access to highly functionalized unsymmetrical aliphatic ketones, which further highlights the utility of this transformation.

  • 7.
    Sanz-Marco, Amparo
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Martinez-Erro, Samuel
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Pauze, Martin
    Gómez-Bengoa, Enrique
    Martín-Matute, Belén
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    An Umpolung Strategy to React Catalytic Enols with NucleophilesManuskript (preprint) (Övrigt vetenskapligt)
  • 8.
    Sanz-Marco, Amparo
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Martinez-Erro, Samuel
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Pauze, Martin
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi. Universidad del PaísVasco/UPV-EHU, Spain.
    Gómez-Bengoa, Enrique
    Martín-Matute, Belén
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    An umpolung strategy to react catalytic enols with nucleophiles2019Ingår i: Nature Communications, ISSN 2041-1723, E-ISSN 2041-1723, Vol. 10, artikel-id 5244Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    The selective synthesis of a-functionalized ketones with two similar enolizable positions can be accomplished using allylic alcohols and iridium(III) catalysts. A formal 1,3-hydrogen shift on allylic alcohols generates catalytic iridium-enolates in a stereospecific manner, which are able to react with electrophiles to yield alpha-functionalized ketones as single constitutional isomers. However, the employment of nucleophiles to react with the nucleophilic catalytic enolates in this chemistry is still unknown. Herein, we report an umpolung strategy for the selective synthesis of alpha-alkoxy carbonyl compounds by the reaction of iridium enolates and alcohols promoted by an iodine(III) reagent. Moreover, the protocol also works in an intra-molecular fashion to synthesize 3(2H)-furanones from gamma-keto allylic alcohols. Experimental and computational investigations have been carried out, and mechanisms are proposed for both the inter- and intramolecular reactions, explaining the key role of the iodine(III) reagent in this umpolung approach.

  • 9.
    Sanz-Marco, Amparo
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Možina, Štefan
    Martinez-Erro, Samuel
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Iskra, Jernej
    Martín‐Matute, Belén
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Synthesis of alpha-Iodoketones from Allylic Alcohols through Aerobic Oxidative Iodination2018Ingår i: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 360, nr 20, s. 3884-3888Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    An efficient method for the synthesis of alpha-iodoketones from allylic alcohols and elemental iodine is reported. We show in this paper that the isomerization of allylic alcohols catalyzed by iridium(III) complexes can be combined with an aerobic oxidative iodination protocol, resulting in a straightforward method for the synthesis of a wide range of alpha-iodoketones as single constitutional isomers and in high yields under mild reaction conditions.

1 - 9 av 9
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