Synthesis of 3-CF3-4-acyl-substituted quinoline derivatives via a cascade reaction of nitrosoarenes and β-CF3-1,3-enynes

Literature Information

Publication Date 2023-11-02
DOI 10.1039/D3QO01208E
Impact Factor 5.281
Authors

Wenhui Li, Shuangping Huang, Qiang Liu, Xing Li, Wenwen Chen


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Abstract

An unprecedented tandem strategy for the construction of an array of 3-CF3-4-acyl functionalized quinolines has been described from readily available nitrosoarenes and β-CF3-1,3-enynes as starting materials by the combined use of Cu(OTf)2 as a catalyst and DMAP as a base. This reaction proceeds via a sequential formation of C–N, C–O and C–C bonds and the steric hindrance effect of substituents (R1) on the benzene ring of nitrosoarenes has a crucial impact on the reaction reactivity and site-selectivity. This cascade transformation features a novel annulation, easy C–H bond activation, readily available starting materials, good step-economy, good site-selectivity, generation of three new bonds and mild reaction conditions.

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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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