Sc(OTf)3/BF3·OEt2-Catalyzed Annulation of 3-Formylchromones with Functionalized Alkenes: Access to Diverse 2-Hydroxybenzophenones,Organic Letters

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Sc(OTf)3/BF3·OEt2-Catalyzed Annulation of 3-Formylchromones with Functionalized Alkenes: Access to Diverse 2-Hydroxybenzophenones
Organic Letters ( IF 4.9 ) Pub Date : 2022-06-09 , DOI: 10.1021/acs.orglett.2c01538
Sabera Sultana ₁ , Peter Yuosef M Rubio ₁ , Hari Datta Khanal ₁ , Yong Rok Lee ₁

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The Sc(OTf)₃/BF₃·OEt₂-catalyzed annulation of 3-formylchromones with functionalized alkenes for the direct construction of 2-hydroxybenzophenones is described. Sc(OTf)₃/BF₃·OEt₂ acts as a synergistic catalyst, providing rapid synthetic access to diversely and highly functionalized 2-hydroxybenzophenones. This reaction has excellent regio- and chemoselectivities and is suitable for late-stage functionalization. The reaction proceeds via [3 + 3] and [4 + 2] cycloaddition processes, through carbonyl-ene, Diels–Alder, or aldol-type reactions. Furthermore, this protocol tolerates the various functional groups present in natural terpenes and steroids.

中文翻译：

Sc(OTf)3/BF3·OEt2 催化 3-甲酰基色酮与官能化烯烃的环化：获得多种 2-羟基二苯甲酮

描述了 Sc(OTf) ₃ /BF ₃ ·OEt ₂催化的 3-甲酰基色酮与官能化烯烃的环化，用于直接构建 2-羟基二苯甲酮。Sc(OTf) ₃ /BF ₃ ·OEt ₂作为一种协同催化剂，可以快速合成多种高度官能化的 2-羟基二苯甲酮。该反应具有优异的区域和化学选择性，适用于后期功能化。该反应通过 [3 + 3] 和 [4 + 2] 环加成过程，通过羰基-烯、Diels-Alder 或醛醇型反应进行。此外，该协议可以容忍天然萜烯和类固醇中存在的各种官能团。

更新日期：2022-06-09

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