B(C6F5)3/Amine‐Catalyzed C(sp)−H Silylation of Terminal Alkynes with Hydrosilanes: Experimental and Theoretical Studies,Angewandte Chemie International Edition

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B(C6F5)3/Amine‐Catalyzed C(sp)−H Silylation of Terminal Alkynes with Hydrosilanes: Experimental and Theoretical Studies
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2018-10-17 , DOI: 10.1002/anie.201809533
Yuanhong Ma ₁ , Shao‐Jie Lou ₂ , Gen Luo ₃ , Yong Luo ₁ , Gu Zhan ₁ , Masayoshi Nishiura _{1,

2} , Yi Luo ₃ , Zhaomin Hou _{1,

2,

3}

Affiliation

Transition metal catalyzed C−H functionalization of organic compounds has proved to be a useful atom‐efficient strategy in organic synthesis. In contrast, main‐group‐element‐based catalytic processes for C−H functionalization have remained underexplored to date. Reported herein is the catalytic C(sp)−H silylation of a wide range of terminal alkynes with hydrosilanes by using a combination of B(C₆F₅)₃ and an organic base such as triethylenediamine (DABCO). This protocol constitutes the first example of boron‐catalyzed C(sp)−H functionalization, offering a convenient route for the synthesis of a variety of alkynylsilanes. Experimental and computational studies have revealed that DABCO plays two crucial roles (Lewis base and Brønsted base) in this catalytic transformation.

中文翻译：

B（C6F5）3 /胺催化末端炔烃与氢硅烷的C（sp）-H硅烷化：实验和理论研究

过渡金属催化的有机化合物的CH官能化已被证明是有机合成中有用的原子效率策略。相比之下，迄今为止，对于CHH功能化的基于主族元素的催化过程仍未得到充分研究。本文报道的是通过使用B（C ₆ F ₅）₃的组合，各种末端炔烃与氢硅烷的催化C（sp）-H甲硅烷基化反应和有机碱，例如三乙二胺（DABCO）。该协议构成了硼催化的C（sp）-H功能化的第一个例子，为合成各种炔基硅烷提供了一条便捷的途径。实验和计算研究表明，DABCO在此催化转化中起着两个至关重要的作用（刘易斯碱和布朗斯台德碱）。

更新日期：2018-10-17

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