期刊
CHEMPLUSCHEM
卷 80, 期 5, 页码 859-864出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cplu.201402426
关键词
chalcones; chemoselectivity; continuous-flow processing; deuteration; heterogeneous catalysis
资金
- National Science Council of Taiwan
- Hungarian Academy of Sciences [NSC 102-2911-I-037-501, SNK-79/2013]
- National Science Council, Taiwan [NSC 98-2323-B-037-004, 99-2323-B-037-002]
- Hungarian Research Foundation [OTKA NK81371, OTKA PD103994]
- Hungarian Academy of Sciences
- [TAMOP-4.2.2/A-11/1/KONV-2012-0035]
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.
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