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Updated: Jan 20, 2026
Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Indium-Catalyzed Synthesis of 4-Alkynyl-2-quinolones Accompanied by Alkyne Migration
1State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, Engineering Research Center of Photoresist Materials, Ministry of Education, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, Jiangsu 210023, China.
Abstract:
A novel synthetic strategy facilitates the assembly of 4-alkynyl-2-quinolones from α-ketoamides equipped with a tethered alkyne. This process is distinguished by an unexpected internal alkyne migration that effectively relocates the alkyne moiety. Mechanistic insight reveals the intervention of a key allene intermediate, whose isomerization furnishes the product. The Lewis acid catalyst is shown to play a dual role in mediating the overall alkyne-allene-alkyne interconversion. The quinolone products themselves might act as versatile synthetic linchpins, providing diversity-oriented access to a range of complex heterocyclic architectures.
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