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Copper‐catalyzed Clauson–Kass pyrroles synthesis in aqueous media
Author(s) -
Deng HongJuan,
Fang YuJing,
Chen GaoWei,
Liu MiaoChang,
Wu HuaYue,
Chen JiuXi
Publication year - 2012
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.1864
Subject(s) - chemistry , aqueous medium , copper , catalysis , selectivity , aqueous solution , combinatorial chemistry , organic chemistry
An efficient and convenient copper‐catalyzed Clauson–Kass reaction of 2,5‐dimethoxytetrahydrofuran with amines in aqueous media has been developed, providing a wide range of N ‐substituted pyrroles in good yields. It is noteworthy that the Clauson–Kass reaction of 2,5‐dimethoxytetrahydrofuran with p ‐phenylenediamine or m ‐phenylenediamine proceeds smoothly to afford the corresponding monopyrroles and bispyrroles with high selectivity in impressive yields. A plausible mechanism for the formation of N ‐substituted pyrroles has been proposed. Copyright © 2012 John Wiley & Sons, Ltd.