Photooxidative Reaction of β-Oxoamides with Amines for the Synthesis of Pyrrolin-4-ones under External Photocatalyst-Free Conditions

作者：Aanuoluwapo O. Oyejobi, Jie Huang, Yun-Xuan Luo, Xiang‐Ying Tang, Long Wang · 发表于：The Journal of Organic Chemistry · 年份：2024 · DOI：10.1021/acs.joc.4c00833 · 被引用次数：7 · 研究领域：Radical Photochemical Reactions、Oxidative Organic Chemistry Reactions、Fluorine in Organic Chemistry

The incorporation of oxygen atoms from air under aerobic conditions plays an important role in organic synthesis. Herein, Brønsted acids are found to be a two-in-one strategic catalyst to transform enamines from β-oxoamides and amines to pyrrolin-4-ones without an external photocatalyst under visible-light conditions. The Brønsted acid can inhibit the C–C bond fragmentation of the [2 + 2] adduct from enamine and 1 O 2, but most importantly, it can form photosensitizers with enamine and pyrrolin-4-one product by acidochromism to promote the 1 O 2 generation.