Calcium-Catalyzed Dehydrogenative Silylation of Aromatic Ethers with Hydrosilane,ACS Catalysis

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Calcium-Catalyzed Dehydrogenative Silylation of Aromatic Ethers with Hydrosilane
ACS Catalysis ( IF 11.3 ) Pub Date : 2021-02-01 , DOI: 10.1021/acscatal.0c05440
Lanxiao Zhao _{1,

2} , Xianghui Shi ₁ , Jianhua Cheng _{1,

2}

Affiliation

The catalytic regioselective C–H silylation of a wide range of alkoxy-substituted benzene derivatives with primary hydrosilane was achieved by the use of scorpionate-supported calcium benzyl complex [(Tp^Ad,iPr)Ca(p-CH₂C₆H₄Me)(THP)] (1) (Tp^Ad,iPr = hydrotris(3-adamantyl-5-isopropylpyrazolyl)borate, THP = tetrahydropyran) as the precatalyst. This protocol offers an atom-efficient and straightforward method for the synthesis of a variety of silyl-substituted aromatic ether derivatives without a hydrogen acceptor and free of transition metal. Calcium anisyl complexes [(Tp^Ad,iPr)Ca(o-MeO-m-Br-C₆H₃)] (5) and [(Tp^Ad,iPr)Ca(o-Me-OCH₂C₆H₄)] (6), proposed as the catalytic reaction intermediates, were isolated and structurally characterized.

中文翻译：

含氢硅烷的钙催化芳香醚的脱氢甲硅烷基化

广泛的烷氧基取代的苯衍生物与伯氢硅烷的催化区域选择性C–H甲硅烷基化是通过使用蝎子酸酯负载的苄基钙钙络合物[（Tp ^{Ad，i Pr}）Ca（p -CH ₂ C ₆ H ₄ Me）（THP）]（1）（Tp ^{Ad，i Pr} =氢三（3-金刚烷基-5-异丙基吡唑基）硼酸酯，THP =四氢吡喃）作前催化剂。该方案提供了一种原子高效且直接的方法，用于合成多种不具有氢受体且不含过渡金属的甲硅烷基取代的芳族醚衍生物。茴香酸钙络合物[（TP ^Ad，iPr）Ca（o -MeO- m- Br-C ₆ H ₃）]（5）和[（Tp ^{Ad，i Pr}）Ca（o -Me-OCH ₂ C ₆ H ₄）]（6）建议分离出催化反应中间体并进行结构表征。

更新日期：2021-02-19

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