Organophotoredox-Catalyzed Intermolecular Formal Grob Fragmentation of Cyclic Alcohols with Activated Allylic Acetates
Wubing Zeng, Xiaoyu Zhang, Yinlei Zhang, Shiji Xiao, Yongming Tang, Peizhong Xie, Teck‐Peng Loh
Abstract
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.
Topics & Concepts
Allylic rearrangementChemistryCatalysisStereoselectivityIntermolecular forceFragmentation (computing)Acetic acidCombinatorial chemistryOrganic chemistryMoleculeOperating systemComputer scienceOxidative Organic Chemistry ReactionsRadical Photochemical ReactionsAlkaloids: synthesis and pharmacology