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Updated: Apr 27, 2026

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
Gold-catalyzed 1,3-transposition of ynones
Roohollah Kazem Shiroodi1, Mohammad Soltani, Vladimir Gevorgyan
1Department of Chemistry, University of Illinois at Chicago , 845 West Taylor Street, Chicago, Illinois 60608-7061, United States.
Abstract:
An efficient, regioselective gold-catalyzed 1,3-transposition reaction of ynones and diynones has been developed. It was found that stereoelectronic (interrupted conjugation) and electronic (extended conjugation) factors could efficiently govern the regioselectivity of this thermodynamically controlled transformation. The produced conjugated diynones were efficiently transformed into diverse alkyne-substituted five- and six-membered heterocycles.
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