Organophotoredox-catalyzed intermolecular formal Grob fragmentation of cyclic alcohols with activated allylic acetates

• Main Authors: Zeng, Wubing, Zhang, Xiaoyu, Zhang, Yinlei, Xiao, Shiji, Tang, Yongming, Xie, Peizhong, Loh, Teck-Peng
• Other Authors: School of Physical and Mathematical Sciences
• Format: Article
• Language: English
• Published: 2023
• Subjects: Science::Chemistry; Grob Fragmentation; Allylation of Cyclic Alcohols
• Online Access: https://hdl.handle.net/10356/171451
• Institution: Nanyang Technological University

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.