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Benzothiophenes

The Experts below are selected from a list of 327 Experts worldwide ranked by ideXlab platform

David J Procter – 1st expert on this subject based on the ideXlab platform

  • Para-coupling of phenols with C2/C3-substituted benzothiophene S-oxides
    Tetrahedron, 2020
    Co-Authors: Zhen He, Gregory J P Perry, Tony Biremond, David J Procter

    Abstract:

    Abstract C2 and C3 substituted Benzothiophenes are common structures in medicinal and materials chemistry. The cross-coupling of phenols with Benzothiophenes is a useful route towards these important molecules. In this report we reveal an efficient C–H/C–H-type cross-coupling of Benzothiophenes, activated as their S-oxides, with phenols to give C2/C3 arylated Benzothiophenes. Whereas previous reports describe cross-coupling at the ortho-position between phenols and sulfoxides, this procedure allows para-functionalization of phenols that typically have their ortho positions blocked.

  • metal free synthesis of Benzothiophenes by twofold c h functionalization direct access to materials oriented heteroaromatics
    Angewandte Chemie, 2019
    Co-Authors: Alexander P Pulis, Gregory J P Perry, David J Procter

    Abstract:

    : Due to their ubiquity in nature and frequent use in organic electronic materials, Benzothiophenes are highly sought after. Here we set out an unprecedented procedure for the formation of Benzothiophenes by the twofold vicinal C-H functionalization of arenes that does not require metal catalysis. This one-pot annulation proceeds through an interrupted Pummerer reaction/[3,3]-sigmatropic rearrangement/cyclization sequence to deliver various benzothiophene products. The procedure is particularly effective for the rapid synthesis of Benzothiophenes from non-prefunctionalized polyaromatic hydrocarbons (PAHs).

  • transition metal free cross coupling of Benzothiophenes and styrenes in a stereoselective synthesis of substituted e z 1 3 dienes
    Angewandte Chemie, 2019
    Co-Authors: Mindaugas Siauciulis, Alexander P Pulis, Nanna Ahlsten, David J Procter

    Abstract:

    : A transition metal-free one-pot stereoselective approach to substituted (E,Z)-1,3-dienes was developed by using an interrupted Pummerer reaction/ligand-coupling strategy. Readily available benzothiophene S-oxides, which can be conveniently prepared by oxidation of the parent Benzothiophenes, undergo Pummerer coupling with styrenes. Reaction of the resultant sulfonium salts with alkyllithium/magnesium reagents generates underexploited hypervalent sulfurane intermediates that undergo selective ligand coupling, resulting in dismantling of the benzothiophene motif and the formation of decorated (E,Z)-1,3-dienes.

Alexander P Pulis – 2nd expert on this subject based on the ideXlab platform

  • metal free synthesis of Benzothiophenes by twofold c h functionalization direct access to materials oriented heteroaromatics
    Angewandte Chemie, 2019
    Co-Authors: Alexander P Pulis, Gregory J P Perry, David J Procter

    Abstract:

    : Due to their ubiquity in nature and frequent use in organic electronic materials, Benzothiophenes are highly sought after. Here we set out an unprecedented procedure for the formation of Benzothiophenes by the twofold vicinal C-H functionalization of arenes that does not require metal catalysis. This one-pot annulation proceeds through an interrupted Pummerer reaction/[3,3]-sigmatropic rearrangement/cyclization sequence to deliver various benzothiophene products. The procedure is particularly effective for the rapid synthesis of Benzothiophenes from non-prefunctionalized polyaromatic hydrocarbons (PAHs).

  • transition metal free cross coupling of Benzothiophenes and styrenes in a stereoselective synthesis of substituted e z 1 3 dienes
    Angewandte Chemie, 2019
    Co-Authors: Mindaugas Siauciulis, Alexander P Pulis, Nanna Ahlsten, David J Procter

    Abstract:

    : A transition metal-free one-pot stereoselective approach to substituted (E,Z)-1,3-dienes was developed by using an interrupted Pummerer reaction/ligand-coupling strategy. Readily available benzothiophene S-oxides, which can be conveniently prepared by oxidation of the parent Benzothiophenes, undergo Pummerer coupling with styrenes. Reaction of the resultant sulfonium salts with alkyllithium/magnesium reagents generates underexploited hypervalent sulfurane intermediates that undergo selective ligand coupling, resulting in dismantling of the benzothiophene motif and the formation of decorated (E,Z)-1,3-dienes.

  • pummerer chemistry of benzothiophene s oxides metal free alkylation and arylation of Benzothiophenes
    Phosphorus Sulfur and Silicon and The Related Elements, 2019
    Co-Authors: Zhen He, Alexander P Pulis, Gregory J P Perry, David J Procter

    Abstract:

    AbstractFunctionalized Benzothiophenes are important constructs found in molecules with wide ranging biological activity and in organic materials. An efficient, metal-free approach to C3 and C2 ary…

Kevin Yang – 3rd expert on this subject based on the ideXlab platform

  • transition metal free synthesis of c3 arylated benzofurans from Benzothiophenes and phenols
    Organic Letters, 2018
    Co-Authors: Kevin Yang, Alexander P Pulis, Gregory J P Perry, David J Procter

    Abstract:

    We report a transition-metal-free synthesis of benzofurans from Benzothiophenes and phenols that exploits the unique reactivity of sulfoxides. Through a sequence involving an interrupted Pummerer reaction and [3,3] sigmatropic rearrangement, phenols can be combined with readily accessible yet synthetically unexplored benzothiophene S-oxides to provide C3-arylated benzofuran products. The products from this approach can undergo subsequent functionalization to gain access to a range of important benzofuran derivatives.

  • synthesis of c2 substituted Benzothiophenes via an interrupted pummerer 3 3 sigmatropic 1 2 migration cascade of benzothiophene s oxides
    Angewandte Chemie, 2018
    Co-Authors: Zhen He, Harry J Shrives, Jose A Fernandezsalas, Alberto Abengozar, Jessica Neufeld, Kevin Yang, Alexander P Pulis, David J Procter

    Abstract:

    : Functionalized Benzothiophenes are important scaffolds found in molecules with wide ranging biological activity and in organic materials. We describe an efficient, metal-free synthesis of C2 arylated, allylated, and propargylated Benzothiophenes. The reaction utilizes synthetically unexplored yet readily accessible benzothiophene S-oxides and phenols, allyl-, or propargyl silanes in a unique cascade sequence. An interrupted Pummerer reaction between benzothiophene S-oxides and the coupling partners yields sulfonium salts that lack aromaticity and therefore allow facile [3,3]-sigmatropic rearrangement. The subsequently generated benzothiophenium salts undergo a previously unexplored 1,2-migration to access C2 functionalized Benzothiophenes.

  • Synthesis of C2 Substituted Benzothiophenes via an Interrupted Pummerer/[3,3]-Sigmatropic/1,2-Migration Cascade of Benzothiophene S-Oxides.
    Angewandte Chemie, 2018
    Co-Authors: Zhen He, Harry J Shrives, Alberto Abengozar, Jessica Neufeld, Kevin Yang, Alexander P Pulis, José A. Fernández-salas, David J Procter

    Abstract:

    : Functionalized Benzothiophenes are important scaffolds found in molecules with wide ranging biological activity and in organic materials. We describe an efficient, metal-free synthesis of C2 arylated, allylated, and propargylated Benzothiophenes. The reaction utilizes synthetically unexplored yet readily accessible benzothiophene S-oxides and phenols, allyl-, or propargyl silanes in a unique cascade sequence. An interrupted Pummerer reaction between benzothiophene S-oxides and the coupling partners yields sulfonium salts that lack aromaticity and therefore allow facile [3,3]-sigmatropic rearrangement. The subsequently generated benzothiophenium salts undergo a previously unexplored 1,2-migration to access C2 functionalized Benzothiophenes.