Construction of 2,3-quaternary fused indolines from alkynyl tethered oximes and diaryliodonium salts through a cascade strategy of N-arylation/cycloaddition/[3,3]-rearrangement,Green Chemistry

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Construction of 2,3-quaternary fused indolines from alkynyl tethered oximes and diaryliodonium salts through a cascade strategy of N-arylation/cycloaddition/[3,3]-rearrangement
Green Chemistry ( IF 9.3 ) Pub Date : 2017-10-31 00:00:00 , DOI: 10.1039/c7gc02844j
Xiao-Pan Ma _{1,

2,

3,

4,

5} , Kun Li _{1,

2,

3,

4,

5} , Si-Yi Wu _{1,

2,

3,

4,

5} , Cui Liang _{1,

2,

3,

4,

5} , Gui-Fa Su _{1,

2,

3,

4,

5} , Dong-Liang Mo _{1,

2,

3,

4,

5}

Affiliation

A variety of 2,3-quaternary fused indolines could be prepared in good yields with high diastereoselectivity from alkynyl tethered oximes and diaryliodonium salts under mild metal-free conditions. The reaction initially goes through a selective N-arylation to provide alkynyl tethered nitrones and regioselectively undergoes an intramolecular (3 + 2) cycloaddition followed by a [3,3]-sigmatropic rearrangement to afford 2,3-quaternary fused indolines in a one-pot fashion. The method features easily available cheap materials, multiple bond formation, gram scalable preparation and diversity of fused indoline scaffolds.

中文翻译：

通过N-芳基化/环加成/ [3,3]-重排的级联策略，从炔烃系肟和二芳基碘鎓盐构建2，3-季稠二氢吲哚

在温和的无金属条件下，可以从炔基系肟和二芳基碘鎓盐以高收率和高非对映选择性制备各种2,3-季稠二氢吲哚。该反应首先通过选择性N-芳基化反应提供炔基束缚的硝酮，然后区域选择性地进行分子内（3 + 2）环加成反应，然后进行[3,3]-σ重排，从而形成2,3-季稠二氢吲哚。锅时尚。该方法的特点是容易获得的廉价材料，多重键的形成，克级可缩放的制备以及熔融的吲哚啉支架的多样性。

更新日期：2017-11-15

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