Gold-Catalyzed Intermolecular Alkyne Oxyarylation for C3 Functionalization of Benzothiophenes

C3-selective C-C bond formation on benzothiophenes is challenging, and few direct functionalization methods are available. A gold-catalyzed reaction of alkynes with benzothiophene S-oxides provides regioselective entry into C3-alkylated benzothiophenes with the C7-alkylated isomer as the minor product. This oxyarylation reaction works with alkyl and aryl alkynes and substituted and unsubstituted benzothiophenes. Mechanistic studies identify that sulfoxide inhibits the catalyst [DTBPAu(PhCN)]SbF6, which also degrades and forms the unreactive complex [(DTBP)(2)Au]SbF6.

Automated summary

Selective C3-alkylation of benzothiophenes was achieved through a gold-catalyzed reaction, with the minor product being the C7-alkylated isomer. The reaction was successful with various alkyl and aryl alkynes and substituted or unsubstituted benzothiophenes, but the inhibitory effect of sulfoxide on the catalyst requires further investigation.