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Silver-catalyzed regioselective 1,6-hydroarylation of para-quinone methides with anilines and phenols
Organic Chemistry Frontiers ( IF 5.4 ) Pub Date : 2022-05-24 , DOI: 10.1039/d2qo00541g
Biquan Xiong 1, 2 , Shipan Xu 1 , Weifeng Xu 1 , Yu Liu 1 , Limin Zhang 2 , Ke-Wen Tang 1 , Shuang-Feng Yin 3 , Wai-Yeung Wong 2
Affiliation  

A simple and efficient method for the silver-catalyzed regioselective 1,6-hydroarylation of para-quinone methides (p-QMs) with anilines and phenols has been established. Without the need for pre-protection, a broad range of anilines (primary amine, secondary amine and tertiary amine), phenols and para-quinone methides are well tolerated under mild conditions, giving the corresponding 1,6-hydroarylation products with moderate to good yields. Moreover, a series of modified natural products can be synthesized via this simple method. Control experiments were also performed to gain insights into the plausible reaction mechanism. This protocol has high atom economy, and may have significant implications for the formation of C(sp3)–C(sp2) bonds in organic synthesis.

中文翻译:

银催化苯胺和苯酚对苯醌甲基化物的区域选择性 1,6-氢化芳基化

建立了一种简单有效的银催化苯胺和苯酚区域选择性1,6-氢化对醌甲基化物( p -QMs ) 的方法。无需预保护,多种苯胺(伯胺、仲胺和叔胺)、苯酚和醌甲基化物在温和条件下具有良好的耐受性,相应的 1,6-氢化芳基化产物具有中等至良好的耐受性产量。此外,通过这种简单的方法可以合成一系列修饰的天然产物。还进行了对照实验以深入了解可能的反应机制。该协议具有较高的原子经济性,可能对 C(sp3 )-C(sp 2 ) 键在有机合成中。
更新日期:2022-05-24
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