Photocatalytic C(sp 3 )–P and C(sp 2 )–P Bond Formation via a Phosphorus Radical Cation

作者：Kui Zhang, Jie Liu, Yan Li, Yi‐Wei Xu, Lingchao Cai · 发表于：Organic Letters · 年份：2024 · DOI：10.1021/acs.orglett.4c03184 · 被引用次数：11 · 研究领域：Radical Photochemical Reactions、Sulfur-Based Synthesis Techniques、Fluorine in Organic Chemistry

A straightforward method for the phosphorylation of electron-deficient alkenes and aryl alkynes has been developed, leading to C(sp 3 )–P and C(sp 2 )–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.