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Visible-light-mediated selective thiocyanation/ipso-cyclization/oxidation cascade for the synthesis of thiocyanato-containing azaspirotrienediones
Tetrahedron ( IF 2.1 ) Pub Date : 2019-11-05 , DOI: 10.1016/j.tet.2019.130763
Yuan Chen , Yu-Jue Chen , Zhi Guan , Yan-Hong He

A visible-light-mediated metal-free thiocyanate radical addition/ipso-cyclization/oxidation cascade reaction for the synthesis of thiocyanato-containing azaspirotrienediones from N-phenylpropynamides is described. Cheap and readily available ammonium thiocyanate was used as a precursor to the thiocyanate free radical, which undergoes a radical addition reaction with the alkyne, followed by selective ipso-cyclization and oxidation to afford the dearomatized products. No product of ortho-cyclization was detected. The reaction completes the synthesis of C–S, C–C, and C=O bonds in one pot, with abundant and renewable air oxygen as the sole sacrificial reagent and oxygen source.



中文翻译:

可见光介导的选择性硫氰化/本位-cyclization /氧化级联含氰硫基azaspirotrienediones的合成

可见光介导的不含金属的硫氰酸盐基加/本位-cyclization /氧化级联含氰硫基azaspirotrienediones的从合成反应Ñ -phenylpropynamides进行说明。便宜和容易获得的硫氰酸铵用作前体硫氰酸自由基,其经历与炔自由基加成反应,然后进行选择性本位-cyclization和氧化,得到脱芳构化产品。没有检测到环化的产物。该反应在一锅中完成了C–S,CC和C = O键的合成,其中大量和可再生的空气氧气是唯一的牺牲试剂和氧气源。

更新日期:2019-11-05
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