Pd-Catalyzed Debenzylation and Deallylation of Ethers and Esters with Sodium Hydride,ACS Catalysis

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Pd-Catalyzed Debenzylation and Deallylation of Ethers and Esters with Sodium Hydride
ACS Catalysis ( IF 11.3 ) Pub Date : 2018-03-05 00:00:00 , DOI: 10.1021/acscatal.8b00185
Yujian Mao ₁ , Ye Liu ₁ , Yanwei Hu ₁ , Liang Wang ₂ , Shilei Zhang ₁ , Wei Wang _{3,

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Affiliation

Herein we demonstrate simply that the addition of Pd(OAc)₂ as a promotor switches the reactivity of a commonly used base NaH to a nucleophilic reductant. The reactivity is engineered into a palladium-catalyzed reductive debenzylation and deallylation of aryl ethers and esters. This operationally simple, mild protocol displays a broad substrate scope and a broad spectrum of functional group tolerance (>50 examples) and high chemoselectivity toward aryl ethers over aliphatic structures. Moreover, the dual reactivity of NaH as a base and a reductant is demonstrated in efficient synthetic elaboration.

中文翻译：

钯催化氢化钠对醚和酯的脱苄基作用和去甲酰化作用

在这里，我们简单地证明，添加Pd（OAc）₂作为促进剂会将常用的碱式NaH的反应性切换为亲核还原剂。反应性被设计成钯催化的芳基醚和酯的还原性脱苄基作用和脱甲酰化作用。该操作简单，温和的方案显示了广泛的底物范围和宽泛的官能团耐受性（> 50个实例），并且对脂族结构上的芳基醚具有高化学选择性。此外，在有效的合成工艺中证明了NaH作为碱和还原剂的双重反应性。

更新日期：2018-03-05

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