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Updated: Jun 9, 2025
![[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)
[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
Published on: May 21, 2019
Chemoselective Cleavage and Transamidation of Tertiary p-Methoxybenzyl Amides under Metal-Free Photoredox Catalysis
Hee-Chan Jeong1, Hyo-Jun Lee1, Keiji Maruoka2,3
1School of Advanced Science and Technology, Kunsan National University, Gunsan 54150, Republic of Korea.
Abstract:
A metal-free and mild cleavage of tertiary p-methoxybenzyl amides (PMB tert-amide) under photoredox conditions is developed using Mes-Acr-Ph+BF4- and Selectfluor to activate the electron-rich benzylic C-H bond of the PMB moiety. The resulting acyl fluoride intermediate is versatile and facilitates a one-pot transamidation of the PMB tert-amide. The value of this protocol is highlighted by performing the chemoselective activation of the PMB tert-amide in bifunctional molecules containing more reactive functionalities than the amide.
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