Synthesis of 2-acyl benzofurans and indoles based on nucleophile-intercepted Meyer–Schuster rearrangement of <i>o</i>-hydroxyphenyl and <i>o</i>-aminophenyl propargylic alcohols
Zhao-Zhao Li, Si-Jing Jiang, Shu-Yun He, Yu‐Ning Gao, Ming Bian, Hui‐Yu Chen, Zhenjiang Liu
Abstract
A new type of nucleophile-intercepted Meyer–Schuster rearrangement mediated by pyridine N -oxide under metal-free conditions using a catalytic amount of acid is disclosed. It enables synthesis of 2-acyl benzofurans and indoles in 56–>99% yields.
Topics & Concepts
ChemistryNucleophilePyridineCatalysisStereochemistryMedicinal chemistryOrganic chemistryCatalytic Alkyne ReactionsAsymmetric Synthesis and CatalysisSynthetic Organic Chemistry Methods