Transition-Metal-Free Synthesis of Symmetrical 1,4-diarylsubstituted 1,3-Diynes By Iodine-Mediated Decarboxylative Homocoupling of Arylpropiolic Acids

• Published in: Tetrahedron letters Vol. 102; p. 153908
• Main Authors: Ghosh, Subhankar, Kumar Chattopadhyay, Shital
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 20-07-2022
• Subjects: 3-diynes; Arylpropiolic Acids; Decarboxylative Homocoupling; Synthetic methods; Transition-Metal-Free; 1; Arylpropiolic Acids; Synthetic methods; Transition-Metal-Free; 3-diynes; Decarboxylative Homocoupling
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2022.153908

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An efficient metal-free method for the synthesis of symmetrical 1,3-diynes through iodine-mediated decarboxylative homocoupling of aryl propiolic acids was developed. This iodine-mediated decarboxylative homocoupling reaction by Csp-Csp bond formation in DMSO underwent smoothly to afford the corresponding 1,4-disubstituted 1,3-dialkynes in good to excellent yields. This operationally simple and environmentally benign protocol avoids the use of sophisticated ligands, additional oxidants and expensive transition metal/reagents.