Organophotoredox-Catalyzed Intermolecular Formal Grob Fragmentation of Cyclic Alcohols with Activated Allylic Acetates

作者：Wubing Zeng, Xiaoyu Zhang, Yinlei Zhang, Shiji Xiao, Yongming Tang, Peizhong Xie, Teck‐Peng Loh · 发表于：Organic Letters · 年份：2023 · DOI：10.1021/acs.orglett.3c02129 · 被引用次数：11 · 研究领域：Oxidative Organic Chemistry Reactions、Radical Photochemical Reactions、Alkaloids: synthesis and pharmacology

We have developed an efficient method that employs organophotoredox-catalyzed relay Grob fragmentation to facilitate the smooth ring-opening allylation of cyclic alcohols in an environmentally friendly manner. This protocol directly incorporates a wide spectrum of cyclic alcohols and activated allylic acetates into the cross-coupling reaction, eliminating the need for metal catalysts. The process yields a variety of distally unsaturated ketones with good to excellent outcomes and stereoselectivity, while acetic acid is the sole byproduct.