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David J. Procter - One of the best experts on this subject based on the ideXlab platform.
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Para-coupling of phenols with C2/C3-substituted Benzothiophene S-oxides
Tetrahedron, 2020Co-Authors: Tony Biremond, Gregory J P Perry, David J. ProcterAbstract: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.
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metal free synthesis of Benzothiophenes by twofold c h functionalization direct access to materials oriented heteroaromatics
Angewandte Chemie, 2019Co-Authors: Alexander P Pulis, Gregory J P Perry, David J. ProcterAbstract:: 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).
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Metal-Free Synthesis of Benzothiophenes by Twofold C–H Functionalization: Direct Access to Materials-Oriented Heteroaromatics
Angewandte Chemie (International ed. in English), 2019Co-Authors: Jiajie Yan, Alexander P Pulis, Gregory J P Perry, David J. ProcterAbstract: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).
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transition metal free cross coupling of Benzothiophenes and styrenes in a stereoselective synthesis of substituted e z 1 3 dienes
Angewandte Chemie, 2019Co-Authors: Mindaugas Siauciulis, Alexander P Pulis, Nanna Ahlsten, David J. ProcterAbstract:: 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.
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pummerer chemistry of Benzothiophene s oxides metal free alkylation and arylation of Benzothiophenes
Phosphorus Sulfur and Silicon and The Related Elements, 2019Co-Authors: Zhen He, Alexander P Pulis, Gregory J P Perry, David J. ProcterAbstract: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...
Alexander P Pulis - One of the best experts on this subject based on the ideXlab platform.
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metal free synthesis of Benzothiophenes by twofold c h functionalization direct access to materials oriented heteroaromatics
Angewandte Chemie, 2019Co-Authors: Alexander P Pulis, Gregory J P Perry, David J. ProcterAbstract:: 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).
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Metal-Free Synthesis of Benzothiophenes by Twofold C–H Functionalization: Direct Access to Materials-Oriented Heteroaromatics
Angewandte Chemie (International ed. in English), 2019Co-Authors: Jiajie Yan, Alexander P Pulis, Gregory J P Perry, David J. ProcterAbstract: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).
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transition metal free cross coupling of Benzothiophenes and styrenes in a stereoselective synthesis of substituted e z 1 3 dienes
Angewandte Chemie, 2019Co-Authors: Mindaugas Siauciulis, Alexander P Pulis, Nanna Ahlsten, David J. ProcterAbstract:: 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.
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pummerer chemistry of Benzothiophene s oxides metal free alkylation and arylation of Benzothiophenes
Phosphorus Sulfur and Silicon and The Related Elements, 2019Co-Authors: Zhen He, Alexander P Pulis, Gregory J P Perry, David J. ProcterAbstract: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...
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Transition metal‐free cross‐coupling of Benzothiophenes and styrenes in a stereoselective synthesis of substituted (E,Z)‐1,3‐dienes
2019Co-Authors: Mindaugas Siauciulis, Alexander P Pulis, Nanna Ahlsten, David J. ProcterAbstract: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
Yue Wang - One of the best experts on this subject based on the ideXlab platform.
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direct construction of 2 3 unsubstituted benzofurans and Benzothiophenes via a metal free catalyzed intramolecular friedel crafts reaction
Organic chemistry frontiers, 2019Co-Authors: Jiawei Huang, Shulin Meng, Xianyu Huang, Zhengwei Yang, Ting Qi, Chao Li, Yue Wang, Baolin LiAbstract:A highly effective and straightforward method for the construction of 2,3-unsubstituted benzofurans and Benzothiophenes by the intramolecular Friedel–Crafts reaction has been developed. This phosphoric acid-catalyzed method exhibits good functional group tolerance for both electron-withdrawing groups and electron-donating groups. We have successfully obtained benzofuran and Benzothiophene derivatives with various substituents, and the yield was up to 94%. The development of this reaction provides a simple and efficient strategy for the construction of benzofuran and Benzothiophene skeleton compounds.
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Direct construction of 2,3-unsubstituted benzofurans and Benzothiophenes via a metal-free catalyzed intramolecular Friedel–Crafts reaction
Organic Chemistry Frontiers, 2019Co-Authors: Jiawei Huang, Shulin Meng, Xianyu Huang, Zhengwei Yang, Yue WangAbstract:A highly effective and straightforward method for the construction of 2,3-unsubstituted benzofurans and Benzothiophenes by the intramolecular Friedel–Crafts reaction has been developed. This phosphoric acid-catalyzed method exhibits good functional group tolerance for both electron-withdrawing groups and electron-donating groups. We have successfully obtained benzofuran and Benzothiophene derivatives with various substituents, and the yield was up to 94%. The development of this reaction provides a simple and efficient strategy for the construction of benzofuran and Benzothiophene skeleton compounds.
Jiawei Huang - One of the best experts on this subject based on the ideXlab platform.
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direct construction of 2 3 unsubstituted benzofurans and Benzothiophenes via a metal free catalyzed intramolecular friedel crafts reaction
Organic chemistry frontiers, 2019Co-Authors: Jiawei Huang, Shulin Meng, Xianyu Huang, Zhengwei Yang, Ting Qi, Chao Li, Yue Wang, Baolin LiAbstract:A highly effective and straightforward method for the construction of 2,3-unsubstituted benzofurans and Benzothiophenes by the intramolecular Friedel–Crafts reaction has been developed. This phosphoric acid-catalyzed method exhibits good functional group tolerance for both electron-withdrawing groups and electron-donating groups. We have successfully obtained benzofuran and Benzothiophene derivatives with various substituents, and the yield was up to 94%. The development of this reaction provides a simple and efficient strategy for the construction of benzofuran and Benzothiophene skeleton compounds.
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Direct construction of 2,3-unsubstituted benzofurans and Benzothiophenes via a metal-free catalyzed intramolecular Friedel–Crafts reaction
Organic Chemistry Frontiers, 2019Co-Authors: Jiawei Huang, Shulin Meng, Xianyu Huang, Zhengwei Yang, Yue WangAbstract:A highly effective and straightforward method for the construction of 2,3-unsubstituted benzofurans and Benzothiophenes by the intramolecular Friedel–Crafts reaction has been developed. This phosphoric acid-catalyzed method exhibits good functional group tolerance for both electron-withdrawing groups and electron-donating groups. We have successfully obtained benzofuran and Benzothiophene derivatives with various substituents, and the yield was up to 94%. The development of this reaction provides a simple and efficient strategy for the construction of benzofuran and Benzothiophene skeleton compounds.
Baolin Li - One of the best experts on this subject based on the ideXlab platform.
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direct construction of 2 3 unsubstituted benzofurans and Benzothiophenes via a metal free catalyzed intramolecular friedel crafts reaction
Organic chemistry frontiers, 2019Co-Authors: Jiawei Huang, Shulin Meng, Xianyu Huang, Zhengwei Yang, Ting Qi, Chao Li, Yue Wang, Baolin LiAbstract:A highly effective and straightforward method for the construction of 2,3-unsubstituted benzofurans and Benzothiophenes by the intramolecular Friedel–Crafts reaction has been developed. This phosphoric acid-catalyzed method exhibits good functional group tolerance for both electron-withdrawing groups and electron-donating groups. We have successfully obtained benzofuran and Benzothiophene derivatives with various substituents, and the yield was up to 94%. The development of this reaction provides a simple and efficient strategy for the construction of benzofuran and Benzothiophene skeleton compounds.