Masuda Ryosuke, Anami Yuki, Kusama Hiroyuki
Department of Chemistry, Faculty of Science, Gakushuin University, 1-5-1, Mejiro, Toshima-ku, Tokyo 171-8588, Japan.
Org Lett. 2024 Sep 27;26(38):8011-8016. doi: 10.1021/acs.orglett.4c02757. Epub 2024 Sep 12.
A novel synthesis of selenoesters and telluroesters based on the reactions of nucleophilic siloxycarbenes, which were generated by the visible-light-induced isomerization of the corresponding aroyl-, heteroaroyl-, or alkenoylsilanes, with electrophilic chalcogen reagents was developed. The use of appropriate selenides or ditellurides/Lewis acids enabled the coupling at temperatures below ambient temperature with a broad substrate scope and high functional-group tolerance. To the best of our knowledge, this is the first example of a synthetic method for selenoesters and telluroesters involving the combination of an acylanion equivalent and cationic chalcogen synthons.
基于可见光诱导相应芳酰基、杂芳酰基或烯酰基硅烷异构化生成的亲核硅氧基卡宾与亲电硫属元素试剂的反应，开发了一种新型硒酸酯和碲酸酯的合成方法。使用合适的硒化物或二碲化物/路易斯酸能够在低于环境温度的条件下进行偶联反应，底物范围广泛且对官能团具有高耐受性。据我们所知，这是涉及酰基阴离子等价物和阳离子硫属元素合成子组合的硒酸酯和碲酸酯合成方法的首个实例。
