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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

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Abstract

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.

Graphical abstract: 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

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Publication details

The article was received on 19 Sep 2017, accepted on 31 Oct 2017 and first published on 31 Oct 2017


Article type: Communication
DOI: 10.1039/C7GC02844J
Citation: Green Chem., 2017, Advance Article
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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

    X. Ma, K. Li, S. Wu, C. Liang, G. Su and D. Mo, Green Chem., 2017, Advance Article , DOI: 10.1039/C7GC02844J

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