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
Julija Visnevska, Sergejs Beļakovs, Edgars Ābele

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
DOI
10.2174/157017812800233769

Visnevska, J., Beļakovs, S., Abele, E. 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, Vol.9, No.4, pp.250-256. ISSN 1570-1786. Available from: doi:10.2174/157017812800233769

Publication language
English (en)