Photoinduced EDA Complexes Enabled C(sp²)-OMe Bond Cleavage and Cyanation of Electron-Rich Arenes.

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-06-27 Epub Date: 2025-06-16 DOI:10.1021/acs.orglett.5c01967

Jun Zhou, Sijia Zhang, Wenjie Liu, Jiaxin Yang, Xi Du, Siping Wei, Xia Zhou, Anping Luo, Bowen Lei

引用次数: 0

Abstract

Herein, an EDA complex enabling C(sp²)-OMe bond cleavage and cyanation was established by using 1,4-dicyanobenzene as both an electron-deficient acceptor and a low-toxicity cyanide source. Mechanistic studies revealed the role of double EDA complexes in forming the cyanide anion and aromatic cation radical intermediate, leading to a diverse array of valuable aryl nitrile derivatives in good to excellent yields. Furthermore, late-stage functionalization of biorelevant compounds and gram-scale synthesis demonstrate the utility of this methodology.

查看原文本刊更多论文

光诱导EDA配合物使富电子芳烃的C(sp2)-OMe键断裂和氰化。

本文利用1,4-二苯甲酸作为缺电子受体和低毒氰化物源，建立了一种能裂解C(sp2)-OMe键和氰化的EDA配合物。机理研究揭示了双EDA配合物在形成氰化物阴离子和芳香族阳离子自由基中间体中的作用，从而产生了各种有价值的芳腈衍生物，收率很高。此外，生物相关化合物的后期功能化和克级合成证明了这种方法的实用性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.

Photoinduced EDA Complexes Enabled C(sp2)-OMe Bond Cleavage and Cyanation of Electron-Rich Arenes.

Abstract

Photoinduced EDA Complexes Enabled C(sp²)-OMe Bond Cleavage and Cyanation of Electron-Rich Arenes.