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Introduction of Ether Groups onto Electron‐Deficient Nitrogen‐Containing Heteroaromatics Using Radical Chemistry under Transition‐Metal‐Free Conditions
Author(s) -
Okugawa Naoki,
Moriyama Katsuhiko,
Togo Hideo
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500584
Subject(s) - chemistry , quinoline , isoquinoline , pyridine , crown ether , tetrahydrofuran , ether , formamide , transition metal , radical , benzoyl peroxide , polymer chemistry , organic chemistry , catalysis , monomer , ion , solvent , polymer
Electron‐deficient nitrogen‐containing heteroaromatics, such as quinoline, isoquinoline, and pyridine, were treated with benzoyl peroxide in dioxane, tetrahydropyran, tetrahydrofuran, diethyl ether, and dipropyl ether at 80 °C to form alkylated nitrogen‐containing heteroaromatics in good yields under transition‐metal‐free conditions. This method was successfully applied to the preparation of lariat aza‐crown ethers using 18‐crown‐6 or 15‐crown‐5 with quinoline and isoquinoline in the presence of benzoyl peroxide in good yields under irradiation conditions with a Hg lamp.