B(C6F5)3‑Catalyzed α,β-Difunctionalization and C–N Bond Cleavage of Saturated Amines with Benzo[c]isoxazoles: Access to Quinoline Derivatives

Herein, we disclose a strategy to realize α,β-difunctionalization and C–N bond cleavage of saturated amines with benzo­[c]­isoxazoles via a B­(C6F5)3-catalyzed consecutive hydrogen-borrowing and [4 + 2] cycloaddition followed by a C–N bond cleavage process. In general, the reactions proceed efficien...

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Veröffentlicht in:Journal of organic chemistry 2022-11, Vol.87 (21), p.14840-14845
Hauptverfasser: He, Yan, Liu, Qimeng, Du, Zihe, Xu, Yanhua, Cao, Lingyu, Zhang, Xinying, Fan, Xuesen
Format: Artikel
Sprache:eng
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Zusammenfassung:Herein, we disclose a strategy to realize α,β-difunctionalization and C–N bond cleavage of saturated amines with benzo­[c]­isoxazoles via a B­(C6F5)3-catalyzed consecutive hydrogen-borrowing and [4 + 2] cycloaddition followed by a C–N bond cleavage process. In general, the reactions proceed efficiently in the absence of any oxidant and metal catalyst to afford a broad range of quinoline derivatives starting from easily accessible substrates in an atom-economical manner.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c01290