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1,1,1,3,3,3-Hexafluoro-2-propanol (HFIP)-promoted regiospecific 1,6-hydroarylation of para-quinone methides with N-heteroarenes: Synthesis of unsymmetrical triarylmethanes
Tetrahedron ( IF 2.1 ) Pub Date : 2024-04-07 , DOI: 10.1016/j.tet.2024.133982
Haiyan Xu , Chongyao Liang , Junyu Zhu , Ying-Guo Liu

In this work, a recyclable and highly regioselective 1,6-hydroarylation of -quinone methides (-QMs) with -heteroarenes has been developed under mild conditions. 1,1,1,3,3,3-Hexafluoro-2-propanol (HFIP) as a solvent plays a significant role in this transformation to achieve a wide assortment of unsymmetrical triarylmethanes with high yields and excellent regioselectivity. This novel reaction is featured a very broad substrate scope and outstanding functional group tolerance and could also be scaled-up. Moreover, this Friedel-Crafts alkylation pathway is further supported by replacing HFIP with trifluoroethanol (TFE) in the control reactions.

中文翻译:

1,1,1,3,3,3-六氟-2-丙醇(HFIP)促进的对醌甲基化物与N-杂芳烃的区域特异性1,6-氢芳基化:不对称三芳基甲烷的合成

在这项工作中,在温和条件下开发了-醌甲基化物(-QM)与-杂芳烃的可回收且高度区域选择性的1,6-氢芳基化。 1,1,1,3,3,3-六氟-2-丙醇 (HFIP) 作为溶剂在这一转化中发挥着重要作用,以高产率和优异的区域选择性获得多种不对称三芳基甲烷。这种新颖的反应具有非常广泛的底物范围和出色的官能团耐受性,并且还可以放大。此外,在对照反应中用三氟乙醇 (TFE) 代替 HFIP 进一步支持了这种 Friedel-Crafts 烷基化途径。
更新日期:2024-04-07
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