Journal
CHINESE JOURNAL OF CHEMISTRY
Volume 39, Issue 1, Pages 50-54Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cjoc.202000494
Keywords
Copper catalysis; Arylcyanation; Asymmetric radical reactions; Styrene; Meerwein arylation
Categories
Funding
- National Nature Science Foundation of China [21532009, 91956202, 21821002, 21790330]
- Science and Technology Commission of Shanghai Municipality [20JC1417000, 19590750400, 17JC1401200]
- strategic Priority Research Program [XDB20000000]
- Key Research Program of Frontier Science [QYZDJSSWSLH055]
- International Partnership Program of the Chinese Academy of Sciences [121731KYSB20190016]
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A copper-catalyzed enantioselective arylcyanation of styrenes using readily available anilines as aryl radical precursors has been developed under mild conditions, providing easy access to chiral 2,3-diaryl propionitriles with moderate to good enantioselectivities. This operationally straightforward reaction demonstrates broad substrate scope and high functional group tolerance, and has been successfully applied to the synthesis of a chiral AIEgen and the estrogen receptor-beta agonist (R)-diarylpropionitrile (DPN).
Main observation and conclusion The first copper-catalyzed enantioselective arylcyanation of styrenes has been developed using readily available anilines as aryl radical precursors under mild conditions, which enables easy access to chiral 2,3-diaryl propionitriles with moderate to good enantioselectivities. This operationally straightforward reaction exhibits broad substrate scope and functional group tolerance. Notably, this method has been applied to the synthesis of chiral AIEgen as well as estrogen receptor-beta agonist (R)-diarylpropionitrile (DPN).
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