Photocatalytic C(sp3)–P and C(sp2)–P Bond Formation via a Phosphorus Radical Cation

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-10-14 DOI:10.1021/acs.orglett.4c03184

Kui Zhang, Jie Liu, Yan Li, Yiwei Xu, Lingchao Cai

引用次数: 0

Abstract

A straightforward method for the phosphorylation of electron-deficient alkenes and aryl alkynes has been developed, leading to C(sp³)–P and C(sp²)–P bond formation. This process involves the generation of phosphorus radical cation intermediates through the photocatalyzed oxidation of ethyl diarylphosphinites. The coupling with electron-deficient alkenes encompasses a variety of heteroaromatics, including pyridine, (benzo)thiazole, and benzoxazole, as well as α,β-unsaturated esters and amides. Impressively, the coupling of radical cations with aryl alkynes demonstrated remarkable regioselectivity, thereby facilitating the synthesis of rare α-aryl vinyl phosphine oxides.

Abstract Image

查看原文本刊更多论文

通过磷自由基阳离子形成光催化 C(sp3)-P 和 C(sp2)-P 键

我们开发出了一种直接的方法来对缺电子的烯烃和芳基炔烃进行磷化，从而形成 C(sp3)-P 和 C(sp2)-P 键。这一过程包括通过光催化氧化乙基二芳基亚磷酸生成磷自由基阳离子中间体。与缺电子烯烃的偶联包括吡啶、（苯并）噻唑、苯并恶唑等多种杂芳烃以及α、β-不饱和酯和酰胺。令人印象深刻的是，自由基阳离子与芳基炔的偶联显示出显著的区域选择性，从而促进了稀有的α-芳基乙烯基膦氧化物的合成。

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.