Quinoline as a Photochemical Toolbox: From Substrate to Catalyst and Beyond

作者：Jianbin Li, Chao‐Jun Li · 发表于：Accounts of Chemical Research · 年份：2025 · DOI：10.1021/acs.accounts.5c00513 · 被引用次数：12 · 研究领域：Radical Photochemical Reactions、Catalytic C–H Functionalization Methods、Sulfur-Based Synthesis Techniques

Conspectus Molecular photochemistry, by harnessing the excited states of organic molecules, provides a platform fundamentally distinct from thermochemistry for generating reactive open-shell or spin-active species under mild conditions. Among its diverse applications, the resurgence of the Minisci-type reaction, a transformation historically reliant on thermally initiated radical conditions, has been fueled by modern photochemical strategies with improved efficiency and selectivity. Consequently, the photochemical Minisci-type reaction ranks among the most enabling methods for C( sp 2 )–H functionalizations of heteroarenes, which are of particular significance in medicinal chemistry for the rapid diversification of bioactive scaffolds. A persistent challenge, however, lies in the efficient generation of radicals and controllable addition to the electron-deficient heteroaromatic systems. In our pursuit of protocols to overcome these limitations, we unexpectedly uncovered the photochemical potential of quinoline, which is a naturally abundant, synthetically accessible, and structurally versatile heteroaromatic scaffold that has long served as a prototypical substrate in Minisci-type chemistry. Guided by this serendipitous insight and our scientific curiosity, we successfully repurposed quinoline and its derivatives not merely as substrates but also as a versatile and systematic photochemical toolbox capable of participating in, mediating, and ultimately catalyzing a broad spect...