Punjajom Kunlayanee, Chonradeenitchakul Sukit, Tummatorn Jumreang, Ruchirawat Somsak, Thongsornkleeb Charnsak
Program on Chemical Sciences, Chulabhorn Graduate Institute, 54 Kamphaeng Phet 6 Laksi, Bangkok, 10210, Thailand.
Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, 54 Kamphaeng Phet 6 Laksi, Bangkok, 10210, Thailand.
Org Lett. 2024 Nov 29;26(47):10066-10071. doi: 10.1021/acs.orglett.4c03012. Epub 2024 Nov 15.
An unprecedented Bi(OTf)-catalyzed reaction between 2-arylisatogens and vinylarenes to yield 2,4-diarylquinolines is reported. The transformation occurred via a Bi-coordination to the embedded anionic nitrone oxygen, which induced a regiospecific stepwise formal [4 + 2]-cycloaddition with vinylarenes to yield a strained tricyclic intermediate, which subsequently extruded gaseous carbon monoxide. -Deoxygenative aromatization ensued to produce 2,4-diarylquinolines. The protocol was applicable to a variety of substrates to produce the quinolines in up to an 89% yield.
报道了一种前所未有的由三氟甲磺酸铋催化的2-芳基异腈酮与乙烯基芳烃之间的反应,该反应生成了2,4-二芳基喹啉。该转化过程是通过铋与嵌入的阴离子硝酮氧配位,诱导与乙烯基芳烃发生区域特异性逐步形式上的[4 + 2]环加成反应,生成一个张力三环中间体,该中间体随后释放出气态一氧化碳。接着进行脱氧芳构化反应生成2,4-二芳基喹啉。该方法适用于多种底物,可高达89%的产率生成喹啉。