Copper-catalyzed tandem A3-coupling–isomerization–hydrolysis reactions of aldehydes and terminal alkynes leading to chalcones

Literature Information

Publication Date 2015-12-29
DOI 10.1039/C5QO00282F
Impact Factor 5.281
Authors

Yingwei Zhao, Qiuling Song


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Abstract

Catalyzed by a simple copper salt, the reaction of an aryl aldehyde and a terminal alkyne in the presence of piperidine delivers the valuable chalcone products, which were rarely found in previous A3 coupling reactions. This reaction can be applied to a wide range of substrates. Mechanistic studies indicate that this reaction experiences a tandem process containing A3 coupling, copper assisted isomerization of propadienamine to allenylamine and subsequent hydrolysis.

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Organic Chemistry Frontiers

Organic Chemistry Frontiers
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Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

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