Acylalkylation of Arynes Generated from o-lodoaryl Triflates with Hydrosilanes and Cesium Fluoride

An efficient method to generate aryne intermediates from o-iodoaryl triflates triggered by triethylsilane and cesium fluoride is disclosed. This method realized the acylalkylation of arynes using easily available o-iodoaryl triflate-type precursors, which was difficult when using conventional nucleophilic activators. A wide range of (hetero)arenes including various fused benzothiazoles were successfully synthesized from o-iodoaryl triflates by virtue of their good accessibility and divergent transformations of aryne intermediates.

Automated summary

An efficient method utilizing triethylsilane and cesium fluoride to generate aryne intermediates from o-iodoaryl triflates has been disclosed, allowing for acylalkylation of arynes using easily accessible precursor. A variety of (hetero)arenes, including fused benzothiazoles, were successfully synthesized from o-iodoaryl triflates due to their good accessibility and diverse transformations of aryne intermediates.