Iridium-Catalyzed Hydrochlorination and Hydrobromination of Alkynes by Shuttle Catalysis.,Angewandte Chemie International Edition

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Iridium-Catalyzed Hydrochlorination and Hydrobromination of Alkynes by Shuttle Catalysis.
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2020-01-16 , DOI: 10.1002/anie.201912803
Peng Yu _{1,

2} , Alessandro Bismuto ₁ , Bill Morandi _{1,

2}

Affiliation

Described herein are two different methods for the synthesis of vinyl halides by a shuttle catalysis based iridium-catalyzed transfer hydrohalogenation of unactivated alkynes. The use of 4-chlorobutan-2-one or tert-butyl halide as donors of hydrogen halides allows this transformation in the absence of corrosive reagents, such as hydrogen halides or acid chlorides, thus largely improving the functional-group tolerance and safety profile of these reactions compared to the state-of-the-art. This method has granted access to alkenyl halide compounds containing acid-sensitive groups, such as tertiary alcohols, silyl ethers, and acetals. The synthetic value of those methodologies has been demonstrated by gram-scale synthesis where low catalyst loading was achieved.

中文翻译：

通过穿梭催化铱催化氢氯化和氢溴化炔烃。

本文描述了通过未活化炔烃的基于铱催化的转移氢卤化的穿梭催化来合成卤乙烯的两种不同方法。使用 4-氯丁烷-2-酮或叔丁基卤化物作为卤化氢的供体，可以在没有腐蚀性试剂（例如卤化氢或酰基氯）的情况下进行这种转化，从而大大提高了官能团耐受性和安全性。这些反应与最先进的反应相比。该方法可以制备含有酸敏感基团的烯基卤化合物，例如叔醇、甲硅烷基醚和缩醛。这些方法的合成价值已通过实现低催化剂负载的克级合成得到证明。

更新日期：2020-01-16

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