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Azole‐Anion‐Based Aprotic Ionic Liquids: Functional Solvents for Atmospheric CO 2 Transformation into Various Heterocyclic Compounds
Author(s) -
Zhao Yanfei,
Wu Yunyan,
Yuan Guangfeng,
Hao Leiduan,
Gao Xiang,
Yang Zhenzhen,
Yu Bo,
Zhang Hongye,
Liu Zhimin
Publication year - 2016
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201600281
Subject(s) - chemistry , ionic liquid , azole , deprotonation , atmospheric pressure , hydroxide , ion , inorganic chemistry , organic chemistry , medicinal chemistry , polymer chemistry , catalysis , antifungal , medicine , oceanography , dermatology , geology
The chemical transformation of atmospheric CO 2 is of great significance yet still poses a great challenge. Herein, azole‐anion‐based aprotic ionic liquids (ILs) were synthesized by the deprotonation of weak proton donors (e.g., 2‐methylimidazole, 4‐methylimidazole, and 2,4‐dimethylimidazole) with tetrabutylphosphonium hydroxide, [Bu 4 P][OH]. We found that these ILs, such as [Bu 4 P][2‐MIm], could activate atmospheric CO 2 through the formation of carbamates. The resultant carbamate intermediates could further react with various types of substrate, including propargylic alcohols, 2‐aminobenzonitriles, ortho ‐phenylenediamines, and 2‐aminothiophenol, thereby producing α ‐alkylidene cyclic carbonates, quinazoline‐2,4(1 H,3 H)‐diones, benzimidazolones, and benzothiazoline, respectively, in moderate‐to‐good yields. Thus, we have achieved the transformation of CO 2 at atmospheric pressure, and we expect this method to open up new routes for the synthesis of various oxygen‐containing heterocyclic compounds under metal‐free conditions.