Copper-catalyzed tandem phosphorylative allenylation/cyclization of 1-(o-aminophenyl)prop-2-ynols with the P(O)–H species: access to C2-phosphorylmethylindoles,Organic Chemistry Frontiers

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Copper-catalyzed tandem phosphorylative allenylation/cyclization of 1-(o-aminophenyl)prop-2-ynols with the P(O)–H species: access to C2-phosphorylmethylindoles
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2020-03-10 , DOI: 10.1039/d0qo00159g
Xiao-Yan Liu _{1,

2,

3,

4,

5} , Yun-Xiang Zou _{1,

2,

3,

4,

5} , Hai-Liang Ni _{5,

6,

7,

8} , Jing Zhang _{1,

2,

3,

4,

5} , Hong-Bo Dong _{1,

2,

3,

4,

5} , Long Chen _{1,

2,

3,

4,

5}

Affiliation

A novel cascade reaction of 1-(o-aminophenyl)prop-2-ynols with the P(O)–H species has been developed, which leads to C2-phosphorylmethylindoles with sequential C–P and C–N bond formation in a single operation. Mechanistic studies suggest that the reaction proceeds via a carbocation initiated tandem phosphorylation/5-exo-dig cyclization, which firstly demonstrates the tandem allene formation/cyclization as a new reaction mode of 1-(o-aminophenyl)prop-2-ynols.

中文翻译：

具有P（O）–H种类的1-（邻氨基苯基）丙-2-炔醇的铜催化串联磷酸化烯丙基化/环化：获得C2-磷酰基甲基吲哚

已开发出一种新型的1-（o-氨基苯基）丙-2-炔醇与P（O）–H的级联反应，从而导致C2-磷酰基甲基吲哚在一个单一的顺序中形成C–P和C–N键操作。机理研究表明，该反应通过碳正离子引发的串联磷酸化/ 5 -exo-dig环化反应进行，这首先证明了串联亚丙基的形成/环化是一种新的1-（邻氨基苯基）丙-2-炔醇反应模式。

更新日期：2020-04-24

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