Premium
Continuous‐Flow Synthesis of Functionalized Phenols by Aerobic Oxidation of Grignard Reagents
Author(s) -
He Zhi,
Jamison Timothy F.
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201310572
Subject(s) - phenols , reagent , chemistry , phenol , oxidation process , aryl , organic chemistry , flow chemistry , aryne , combinatorial chemistry , chemical engineering , catalysis , alkyl , engineering
Abstract Phenols are important compounds in chemical industry. An economical and green approach to phenol preparation by the direct oxidation of aryl Grignard reagents using compressed air in continuous gas‐liquid segmented flow systems is described. The process tolerates a broad range of functional groups, including oxidation‐sensitive functionalities such as alkenes, amines, and thioethers. By integrating a benzyne‐mediated in‐line generation of arylmagnesium intermediates with the aerobic oxidation, a facile three‐step, one‐flow process, capable of preparing 2‐functionalized phenols in a modular fashion, is established.