19061-38-2Relevant articles and documents
Acylalkylation of Arynes Generated from o-Iodoaryl Triflates with Hydrosilanes and Cesium Fluoride
Minoshima, Mai,Uchida, Keisuke,Nakamura, Yu,Hosoya, Takamitsu,Yoshida, Suguru
supporting information, p. 1868 - 1873 (2021/03/08)
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.
One-Pot Generation of Functionalized Benzynes from Readily Available 2-Hydroxyphenylboronic Acids
Ikawa, Takashi,Sun, Jingkai,Takagi, Akira,Akai, Shuji
, p. 3383 - 3392 (2020/03/10)
We developed a one-pot method for the generation of benzynes from a range of readily available 2-hydroxyphenylboronic acids. This method features the in situ activation of both boronic acid and hydroxyl groups of the substrate to enhance benzyne generation at 60 °C. Such mild conditions facilitate the generation of functionalized benzynes that immediately react with diverse arynophiles to produce multisubstituted fused benzenes.
Synthesis of 9,10-Diarylanthracenes via Mg(TMP) 2 ·2LiCl-Mediated Benzyne Generation/[4+2] Cycloaddition and Deoxygenation of 9,10-Epoxyanthracene Intermediates
Miyamoto, Naoya,Nakazawa, Yuki,Nakamura, Takanori,Okano, Kentaro,Sato, Sota,Sun, Zhe,Isobe, Hiroyuki,Tokuyama, Hidetoshi
supporting information, p. 513 - 518 (2017/12/08)
A new synthetic route to functionalized 9,10-diarylanthracenes has been developed. 9,10-Epoxyanthracene intermediates were prepared by [4+2] cycloaddition of 1,3-diarylisobenzofuran with a variety of functionalized benzyne intermediates, which were obtained by Mg(TMP) 2 ·2LiCl-mediated benzyne generation. For the cleavage of the resultant 9,10-epoxyanthracene intermediates, we developed mild deoxygenation conditions using a combination of trifluoroacetic acid and Et 3 SiH. The utility of this sequence was demonstrated by application to the synthesis of 5,7,12,14-tetraphenylpentacene.