近日，常州大学药学院王佳胤团队研究了在无金属和光敏剂的条件下，烯炔酮与二芳基硒化物光催化环氧化制备双硒取代的1-茚酮。相关论文于2025年4月17日发表在《中国化学》杂志上。

研究组开发了一种实用的光催化环化双硒烯基化策略，用于在无光敏剂的条件下，以烯炔酮和二芳基硒化物为原料，高效合成双硒取代的1-茚酮（共38个实例），产率通常很高（高达95%），立体选择性优异（>19:1 Z/E比）。反应机理涉及一个级联过程，包括均裂裂解、自由基加成、5-外环化和自由基捕获，从而能够顺序形成多个键，如C（sp₃）-Se、C（sp²）-C（sp³，sp²）-Se键，快速构建分子复杂性。

值得注意的是，这种方法显示出广泛的底物相容性和对各种官能团的优异耐受性。它的另一个特点是在形成化学键和实现100%的高原子利用率方面具有显著的效率。

附：英文原文

Title: Photocatalyzed Annulation-Biselenylation of Enynone with Diarylselenides toward Biselenium-Substituted 1-Indanones under Metal- and Photosensitizer-Free Conditions

Author: Hang-Dong Zuo, Hua-Feng Yan, Yu-Ting Wang, Sheng-Hu Yan, Cheng Guo, Yue Zhang, Jia-Yin Wang

Issue&Volume: 2025-04-17

Abstract: A practical photocatalytic annulation-biselenylation strategy has been developed for the efficient synthesis of biselenium-substituted 1-indanones (38 examples in total) with generally good yields (up to 95%) and excellent stereoselectivity (>19 : 1 Z/E ratio) by employing enynones and diaryl selenides as starting materials under photosensitizer-free conditions. The reaction mechanism involves a cascade process comprising homolytic cleavage, radical addition, 5-exo-dig cyclization, and radical capture, enabling sequential formation of multiple bonds, such as C(sp3)-Se, C(sp3)-C(sp2), and C(sp2)-Se bonds, to rapidly construct molecular complexity. Notably, this approach demonstrates wide substrate compatibility and excellent tolerability towards various functional groups. It is further characterized by its remarkable efficiency in creating chemical bonds and achieving high atomic utilization of 100%.

DOI: 10.1002/cjoc.70018

Source: https://onlinelibrary.wiley.com/doi/full/10.1002/cjoc.70018