Bimetallic Pd/Cu-Catalyzed Sonogashira Coupling-Elimination Reaction: An Efficient Synthesis of 2-Unsubstituted Terminal 1, 3-Enynes

Bimetallic Pd/Cu-Catalyzed Sonogashira Coupling-Elimination Reaction: An Efficient Synthesis of 2-Unsubstituted Terminal 1, 3-Enynes
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DOI:
10.1002/ajoc.202300129
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发表时间:
2023-05-12
影响因子:
2.7
通讯作者:
Xiong,Jie
Xiong,Jie
中科院分区:
化学3区
文献类型:
--
作者:
Shi,Yijun;Sun,Xinyue;Xiong,Jie

文献摘要

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本文报道了一种通过Pd/Cu催化的碘苯与4-溴丁-1-炔的Sonogashira偶联-消除反应高产率合成2-未取代的末端1,3-烯炔的有效策略。据我们所知,这是首次报道4-溴丁-1-炔作为有效的1,3-烯炔试剂,该方法比其他报道的合成方法更方便和成本效益高,这些方法受到起始原料制备费力,溴乙烯成本高以及气体乙炔处理不便的阻碍。
Herein, an efficient strategy to synthesize 2‐unsubstituted terminal 1, 3‐enynes in high yields by bimetallic Pd/Cu‐catalyzed Sonogashira coupling‐elimination reaction of iodobenzenes with 4‐bromobut‐1‐yne was reported. To our knowledge, this is the first report of 4‐bromobut‐1‐yne as an efficient 1, 3‐enynes reagent, and the method is more convenient and cost‐effective than other reported synthetic methods, which are hindered by the laborious preparation of starting materials, the high cost of bromoethene, and the inconvenient handling of gas acetylene.