Photo-on-Demand Synthesis of Vilsmeier Reagents with Chloroform and Their Applications to One-Pot Organic Syntheses
作者:Fengying Liang、Kazuo Eda、Takashi Okazoe、Akihiro Wada、Nobuaki Mori、Katsuhiko Konishi、Akihiko Tsuda
DOI:10.1021/acs.joc.1c00334
日期:2021.5.7
The Vilsmeier reagent (VR), first reported a century ago, is a versatile reagent in a variety of organic reactions. It is used extensively in formylation reactions. However, the synthesis of VR generally requires highly toxic and corrosive reagents such as POCl3, SOCl2, or COCl2. In this study, we found that VR is readily obtained from a CHCl3 solution containing N,N-dimethylformamide or N,N-dimethylacetamide
Vilsmeier试剂(VR)于一个世纪前首次报道,是一种用于多种有机反应的多功能试剂。它被广泛用于甲酰化反应中。然而,VR的合成通常需要剧毒和腐蚀性试剂,例如POCl 3,SOCl 2或COCl 2。在这项研究中,我们发现在O 2鼓泡下进行光辐照后,VR很容易从含有N,N-二甲基甲酰胺或N,N-二甲基乙酰胺的CHCl 3溶液中获得。通过产生气态HCl和CO 2可以高收率获得相应的Vilsmeier试剂作为副产物,以使其分离为适合通过X射线晶体学分析的结晶固体产物。利用使用双功能充当反应物和溶剂的CHCl 3的优点,这种按需光敏VR合成可用于一锅合成醛,酰氯,甲酸酯,酮,酯和酰胺。