Department of Chemistry, FRQNT Center for Green Chemistry and Catalysis, McGill University, 801 Sherbrooke Street West, Montreal, Quebec, Canada H3A 0B8.
Nat Commun. 2015 Mar 10;6:6526. doi: 10.1038/ncomms7526.
Methods to assemble alkynes are essential for synthesizing fine chemicals, pharmaceuticals and polymeric photo-/electronic materials. Using light as a clean energy form and water as a green solvent has the potential to make synthetic chemistry more environmentally friendly. Here we present a transition-metal-free coupling protocol between aryl alkyne and alkyl iodide enabled by photoenergy in water. Under ultraviolet irradiation and in basic aqueous media, aryl alkynes efficiently couple with a wide range of alkyl iodides including primary, secondary and tertiary ones under mild conditions. A tentative mechanism for the coupling is also proposed.
炔烃的偶联方法对于合成精细化学品、药物和聚合光电材料至关重要。利用光作为清洁能源形式和水作为绿色溶剂，有可能使合成化学更加环保。在这里，我们提出了一种在水中通过光能实现的芳基炔烃和碘代烷烃之间的无过渡金属偶联方案。在紫外光照射下，在碱性水介质中，芳基炔烃可以在温和的条件下与包括伯、仲和叔碘代烷烃在内的多种烷基碘代烷烃高效偶联。同时还提出了一个可能的偶联反应机制。
