Alkyne/thio umpolung tactic replacement: synthesis of alkynyl sulfides via capturing the in situ formed alkynylthiolate anion

Abstract

Alkynyl sulfides are prevalent in bioactive molecules and functional materials. A variety of methods for the construction of alkynyl sulfides have been developed, however, the general and practical synthetic strategy...

Cobalt-catalyzed cross-electrophile coupling of alkynyl sulfides with unactivated chlorosilanes

“…Easily synthesized and air-stable alkynyl sulfides 37 , 38 had sporadically been utilized as alkynyl electrophiles for metal catalyzed cross-coupling 39 , 40 , while was unknown for XEC. In this report, we disclose a highly efficient cobalt-catalyzed cross-electrophile alkynylation of a broad range of unactivated chlorosilanes with alkynyl sulfides as a stable and practical alkynyl electrophiles (Fig.…”

Copper-Catalyzed Synthesis of Quinoline-4-thiols from Diaryliodonium Salts, Alkynyl Sulfides, and Nitriles

“…However, the alkyne scope was mainly limited to symmetric alkynes, ynamides, and aryl-alkyl alkynes, which resulted in the desired quinoline products being challenging for further functionalization at position 4. As our continuous interest in the transformation of alkynyl sulfides, we report herein a three-component cascade cyclization among diaryliodonium salts, alkynyl sulfides, and nitriles to synthesize 4-thio-substituted quinolines, in which the thiol group could be further converted into various functional groups at the ipso- position and serve as a directing group for C–H functionalization (Scheme b).…”