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取代苯并[]芴的直接光化学合成

Direct Photochemical Synthesis of Substituted Benzo[]fluorenes.

作者信息

Crawford Ruairi, Ortin Yannick, Twamley Brendan, Baumann Marcus

机构信息

School of Chemistry, University College Dublin, Dublin 4, Ireland.

School of Chemistry, Trinity College Dublin, Dublin 2, Ireland.

出版信息

Org Lett. 2024 Dec 6;26(48):10364-10368. doi: 10.1021/acs.orglett.4c03978. Epub 2024 Nov 24.

Abstract

We report a new and straightforward route toward substituted benzo[]fluorenes via the direct photochemical conversion of alkynylated chalcones. This transformation exploits a high-power light-emitting diode emitting ultraviolet A light to enable the rapid formation of the target products ( = 5 min). A continuous flow approach thereby facilitates reproducibility and scalability, granting streamlined access to these important scaffolds and their derivatives. A mechanistic proposal based on a biradical species is presented and supported by deuteration studies.

摘要

我们报道了一种通过炔基化查耳酮的直接光化学转化制备取代苯并[]芴的新的简便方法。这种转化利用发射紫外线A光的高功率发光二极管,能够快速形成目标产物(=5分钟)。连续流动方法从而促进了可重复性和可扩展性,为获得这些重要骨架及其衍生物提供了简化途径。提出了一种基于双自由基物种的机理假设,并得到了氘代研究的支持。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aceb/11629382/a338ab0f11e3/ol4c03978_0001.jpg

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