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Highly Selective Continuous‐Flow Synthesis of Potentially Bioactive Deuterated Chalcone Derivatives
Author(s) -
Hsieh ChiTing,
Ötvös Sándor B.,
Wu YangChang,
Mándity István M.,
Chang FangRong,
Fülöp Ferenc
Publication year - 2015
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.201402426
Subject(s) - chalcone , chemistry , reagent , combinatorial chemistry , flow chemistry , selectivity , catalysis , deuterium , continuous flow , organic chemistry , biochemical engineering , physics , quantum mechanics , engineering
The selective synthesis of various dideuterochalcones as potentially bioactive deuterium‐labeled products is presented, by means of the highly controlled partial deuteration of antidiabetic chalcone derivatives. The benefits of continuous‐flow processing in combination with on‐demand electrolytic D 2 gas generation has been exploited to avoid over‐reaction to undesired side products and to achieve selective deuterium addition to the carbon–carbon double bond of the starting enones without the need for unconventional catalysts or expensive special reagents. The roles of pressure, temperature, and residence time proved crucial for the fine‐tuning of the sensitive balance between the product selectivity and the reaction rate. The presented flow‐chemistry‐based deuteration technique lacks most of the drawbacks of the classical batch methods, and is convenient, time‐ and cost‐efficient, and safe.