Bi(OTf)(3)-Catalyzed Cascade Cycloaddition-Decarbonylation-N-Deoxygenative Aromatization between 2-Arylisatogens and Styrenes: Unveiling a Synthesis of 2,4-Diarylquinolines

Bi(OTf)3 催化的 2-芳基异噻唑啉与苯乙烯的级联环加成-脱羰-N-脱氧芳构化反应:揭示 2,4-二芳基喹啉的合成

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Abstract

An unprecedented Bi(OTf)(3)-catalyzed reaction between 2-arylisatogens and vinylarenes to yield 2,4-diarylquinolines is reported. The transformation occurred via a Bi(III)-coordination to the embedded anionic nitrone oxygen, which induced a regiospecific stepwise formal [4 + 2]-cycloaddition with vinylarenes to yield a strained tricyclic intermediate, which subsequently extruded gaseous carbon monoxide. N-Deoxygenative aromatization ensued to produce 2,4-diarylquinolines. The protocol was applicable to a variety of substrates to produce the quinolines in up to an 89% yield.

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