Chemoselective Cleavage and Transamidation of Tertiary <i>p</i>-Methoxybenzyl Amides under Metal-Free Photoredox Catalysis
Hee-Chan Jeong, Hyo‐Jun Lee, Keiji Maruoka
Abstract
A metal-free and mild cleavage of tertiary p -methoxybenzyl amides (PMB tert -amide) under photoredox conditions is developed using Mes-Acr-Ph + BF 4 – 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.
Topics & Concepts
ChemistryCleavage (geology)CatalysisPhotoredox catalysisCombinatorial chemistryMetalStereochemistryOrganic chemistryPhotocatalysisFracture (geology)EngineeringGeotechnical engineeringRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesSynthesis and Catalytic Reactions