Dual Activation of Enals and γ-C(sp3)-H Bond of p-Quinols for the Synthesis of Naphthylamines via Cyclization/Dual Aromatization
Junsheng Zhi , Liping Deng , Weijie Huang , Long Sun , Lou Shi , Yifei Li , Qun Liu , Ling Pan
Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (20) : 2630 -2636.
Dual Activation of Enals and γ-C(sp3)-H Bond of p-Quinols for the Synthesis of Naphthylamines via Cyclization/Dual Aromatization
The synthesis of fused arenes from non-aromatic precursors is useful but challenging. Herein, the synthesis of widely-used naphthylamines was focused. The three-component reactions of p-quinols, enals and amines were investigated under the dienamine/iminium- based dual organocatalysis. The efficient synthesis of naphthylamines was achieved via a formal [3+3] cyclization of the amines activated p-quinols and enals, with the following Bu4NOAc/AgNO3 facilitated dual aromatization. The different reactivity of in-situ generated dienamine and iminium intermediates resulted in the differentiating catalysis, providing an efficient and practical methodology for the synthesis of fused arenes from non-aromatic precursors.
Synthetic methods / Organocatalysis / Cyclization / Co-activation / γ-C(sp3)-H activation / Aromatization
2025 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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