稠合二乙炔基苯和菲炔与炔基硅烷。

Fused diethynylbenzenes and phenanthrenes arynes with alkynylsilanes.

作者信息

Dong Jie, Lei Yu, Hu Qiong, Zong Lingli, Zhang Ke, Zhang Yajuan, Hu Yimin

机构信息

Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Key Laboratory of Molecular-Based Materials, School of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000, China.

出版信息

Org Biomol Chem. 2023 Mar 29;21(13):2715-2719. doi: 10.1039/d2ob02046g.

DOI:10.1039/d2ob02046g

PMID:36722919

Abstract

A method for the hydroalkynylation and catalytic cyclization reactions of hexadehydro-Diels-Alder-derived benzynes is described. Diethynylbenzene derivatives are generated in a one-step reaction trimethylsilyl-alkyne groups with benzyne formed by heating the appropriate tetrayne substrate. Trimethyl(phenylethynyl)silane loses TMS and binds to the electron-deficient site on HDDA-derived benzynes, and then phenanthrene was synthesized under mild reaction conditions by transition-metal-free, base promoted intramolecular cyclization.

摘要

描述了一种用于十六脱氢 - 狄尔斯 - 阿尔德衍生的苯炔的氢炔基化和催化环化反应的方法。通过加热适当的四炔底物，使三甲基甲硅烷基 - 炔基与苯炔在一步反应中生成二乙炔基苯衍生物。三甲基（苯乙炔基）硅烷失去三甲基硅基并与十六脱氢 - 狄尔斯 - 阿尔德衍生的苯炔上的缺电子位点结合，然后在温和的反应条件下通过无过渡金属、碱促进的分子内环化反应合成菲。