ortho-[1-(p-MeOPhenyl)vinyl]benzoate PMPVB as a recyclable auxiliary for C–O and C–S bond formation reactions under Brønsted acid catalysis,Organic & Biomolecular Chemistry

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ortho-[1-(p-MeOPhenyl)vinyl]benzoate PMPVB as a recyclable auxiliary for C–O and C–S bond formation reactions under Brønsted acid catalysis
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2023-07-05 , DOI: 10.1039/d3ob00839h
Sangay Moktan ₁ , Mahendra K V Rotta ₁ , Suvendu Halder ₁ , Priyanka Pradhan ₁ , Pavan K Kancharla ₁

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A practically simple and useful method is reported for the synthesis of ethers and thioethers via Brønsted acid-catalyzed activation of ortho-[1-(p-MeOphenyl)vinyl]benzoate (PMPVB) donors derived from alcohols. The mechanism of action is based on the remote activation of an active alkene followed by intramolecular 5-exo-trig cyclization leading to a reactive intermediate that can react via a substrate dependent S_N1 or S_N2 mechanism with alcohols and thiol nucleophiles providing facile access to ether and thioether functionalities, respectively.

中文翻译：

邻-[1-(对甲基苯基)乙烯基]苯甲酸酯 PMPVB 作为布朗斯台德酸催化下 C-O 和 C-S 键形成反应的可回收助剂

报道了一种实用简单且有用的方法，通过布朗斯台德酸催化活化源自醇的邻-[1-(对-MeO苯基)乙烯基]苯甲酸酯(PMPVB)供体来合成醚和硫醚。作用机制基于活性烯烃的远程活化，然后进行分子内 5-外触发环化，产生反应性中间体，该中间体可以通过底物依赖性 S _N 1 或 S _N 2 机制与醇和硫醇亲核试剂反应，从而提供容易的反应。分别获得醚和硫醚官能团。

更新日期：2023-07-05

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