A CO2-Mediated Conjugate Cyanide Addition to Chalcones

被引:7
|
作者
Dotzauer, Simon [1 ]
Hadaf, Gul Barg [1 ]
Kamounah, Fadhil S. [1 ]
Kadziola, Anders [1 ]
Lee, Ji-Woong [1 ]
机构
[1] Univ Copenhagen, Dept Chem, Universitetsparken 5, DK-2100 Copenhagen, Denmark
关键词
carbon dioxide; cyanide; nitriles; catalysis; heterocycles; 1,4-ADDITION; CYANOHYDRIN; ALDEHYDES; ENONES;
D O I
10.3390/catal10121481
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Carbon dioxide is an intrinsically stable molecule; however, it can readily react with various nucleophilic reagents. In the presence of a cyanide source, CO2 was proven to be useful to promote addition reactions. Here we report the use of CO2 to facilitate 1,4-conjugate cyanide addition reaction to chalcones to generate organonitriles. Nitriles are key component in organic synthesis due to their utility in numerous functional group transformation, however, conjugation addition of cyanide has been a challenge in this substrate class due to side reactions. To mitigate this, we employed simple ammonium and metal cyanide sources as nucleophiles under carbon dioxide atmosphere where high selectivity toward the desired product was obtained. The presented reaction is not feasible under inert atmosphere, which highlights the important role of CO2, as a Lewis and Brondsted acidic catalyst. Further derivatization of organonitriles compounds were performed to showcase the utility of the reaction, while an unprecedented dimerization reaction was identified and characterized, affording a cyclopentanone scaffold.
引用
收藏
页码:1 / 9
页数:9
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