Journal
ORGANIC LETTERS
Volume 23, Issue 5, Pages 1868-1873Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c00279
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Funding
- JSPS KAKENHI [JP19K05451, JP18H02104]
- Naito Foundation
- Japan Agency for Medical Research and Development (AMED) [JP20am0101098]
- Cooperative Research Project of Research Center for Biomedical Engineering
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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.
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.
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