Kishida Satoshi, Takano Misaki, Sekiya Takuya, Ukaji Yutaka, Endo Kohei
Department of Chemistry, Faculty of Science, Tokyo University of Science, Tokyo 162-8601, Japan.
Division of Material Chemistry, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192, Japan.
J Org Chem. 2022 Nov 4;87(21):14833-14839. doi: 10.1021/acs.joc.2c01261. Epub 2022 Oct 6.
This paper describes a synthetic approach to the synthesis of 1,2,4,5-tetraarylbenzene derivatives from cyclopropenes. The Lewis acid-mediated dimerization of cyclopropenes gives tricyclo[3.1.0.0]hexane derivatives. The subsequent thermal ring-opening reaction under solvent-free conditions gives 1,4-cyclohexadienes bearing quaternary carbons. The novel Br-mediated oxidative rearrangement of 1,4-cyclohexadienes takes place to give 1,2,4,5-tetraarylbenzene derivatives in high to excellent yields.
本文描述了一种由环丙烯合成1,2,4,5-四芳基苯衍生物的合成方法。环丙烯在路易斯酸介导下二聚生成三环[3.1.0.0]己烷衍生物。随后在无溶剂条件下进行热开环反应，得到带有季碳的1,4-环己二烯。1,4-环己二烯发生新颖的溴介导的氧化重排反应，以高至优异的产率得到1,2,4,5-四芳基苯衍生物。
