Chemoselective Approach to Versatile Acyl Fluorides by Photoinduced Activation of p-Methoxybenzyl Esters
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 new strategy for the metal-free photoinduced activation of p-methoxybenzyl esters is developed using Selectfluor and benzil for the generation of acyl fluoride intermediates that enable various transformations. The highlight of this activation method is its high chemoselectivity in the presence of other functionalities, such as esters, amides, and ketones. A synthetic application for the preparation of peptide mimetics that possess two different amide units is also described.
More Related Videos
08:43Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
06:31Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
Published on: November 27, 2015
Related Concept Videos
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism
Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene
Acid Halides to Esters: Alcoholysis
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis
