3,4-Dihalo-2(5H)-furanones: a novel oxidant for the Glaser coupling reaction

摘要

5-Alkoxy-3,4-dihalo-2(5H)-furanones could be used as a kind of novel oxidant in the Glaser coupling reaction. The screening of reaction conditions showed that both PdCl2(PPh3)2 and 3,4-dichloro-5-methoxy-2(5H)-furanone played crucial roles in the reaction. A possible reaction mechanism was proposed according to the reactivity of 3,4-dihalo-2(5H)-furanones. The new method easily allows the syntheses of alkyl and aryl substituted 1,3-diyne compounds. However, carbyne polymer was unexpectedly obtained when using trimethylsilyl acetylene as the substrate under the Glaser reaction condition.