A Highly Stereoselective Synthesis of E-(But-1-en-3-yne-1-sulfonyl) hetarenes and Disubstituted 2-Benzothiazolyl Alkynes by Palladium Catalyzed Sonogashira Type Coupling of 2-Chlorovinylsulfones

Julija Visnevska, Sergey Belyakov, Edgars Abele

doi:10.2174/157017812800233769

Abstract

Novel and highly stereoselective route to E-(but-1-en-3-yne-1-sulfonyl)hetarenes by palladium catalyzed Sonogashira type coupling of unstable E-2-chlorovinylsulfonylbenzene and E-2-(2-chlorovinylsulfonyl)pyridine was presented. Usage of potassium phosphate as novel base in Sonogashira reaction was demonstrated. Unusual coupling products in the Sonogashira reaction of E-2-(2-chlorovinylsulfanyl)benzothiazole with different alkynes were obtained.

Keywords: Copper catalysis, E-2-chlorovinylsulfonylhetarenes, E-(but-1-en-3-yne-1-sulfonyl)hetarenes, Palladium catalysis, Sonogashira coupling, dendrimers, triethylamine, salts, atom-numbering, atoms

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Letters in Organic Chemistry

Title:A Highly Stereoselective Synthesis of E-(But-1-en-3-yne-1-sulfonyl) hetarenes and Disubstituted 2-Benzothiazolyl Alkynes by Palladium Catalyzed Sonogashira Type Coupling of 2-Chlorovinylsulfones

Volume: 9 Issue: 4

Author(s): Julija Visnevska, Sergey Belyakov, Edgars Abele

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Abstract: Novel and highly stereoselective route to E-(but-1-en-3-yne-1-sulfonyl)hetarenes by palladium catalyzed Sonogashira type coupling of unstable E-2-chlorovinylsulfonylbenzene and E-2-(2-chlorovinylsulfonyl)pyridine was presented. Usage of potassium phosphate as novel base in Sonogashira reaction was demonstrated. Unusual coupling products in the Sonogashira reaction of E-2-(2-chlorovinylsulfanyl)benzothiazole with different alkynes were obtained.

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Julija Visnevska, Sergey Belyakov, Edgars Abele , A Highly Stereoselective Synthesis of E-(But-1-en-3-yne-1-sulfonyl) hetarenes and Disubstituted 2-Benzothiazolyl Alkynes by Palladium Catalyzed Sonogashira Type Coupling of 2-Chlorovinylsulfones , Letters in Organic Chemistry 2012; 9 (4) . https://dx.doi.org/10.2174/157017812800233769