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

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

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 allyl...

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Bibliographic Details
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
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Institution: Nanyang Technological University
Language: English
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Summary: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.

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