External oxidant-free electrooxidative [3 + 2] annulation between phenol and indole derivatives

Intermolecular [3 + 2] annulation is one of the most straightforward approaches to construct five membered heterocycles. However, it generally requires the use of functionalized substrates. An ideal reaction approach is to achieve dehydrogenative [3 + 2] annulation under oxidant-free conditions. Her...

Full description

Saved in:
Bibliographic Details
Published in:Nature communications 2017-10, Vol.8 (1), p.775-8, Article 775
Main Authors: Liu, Kun, Tang, Shan, Huang, Pengfei, Lei, Aiwen
Format: Article
Language:English
Subjects:
639/638/549/933
639/638/77/886
639/638/77/888
Catalysts
Chemical reactions
Chemical synthesis
Cross coupling
Dehydrogenation
Electrochemical oxidation
Electrochemistry
Humanities and Social Sciences
Indoles
multidisciplinary
Organic chemistry
Oxidants
Oxidation
Oxidizing agents
Phenols
Science
Science (multidisciplinary)
Substrates
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Intermolecular [3 + 2] annulation is one of the most straightforward approaches to construct five membered heterocycles. However, it generally requires the use of functionalized substrates. An ideal reaction approach is to achieve dehydrogenative [3 + 2] annulation under oxidant-free conditions. Here we show an electrooxidative [3 + 2] annulation between phenols and N- acetylindoles under undivided electrolytic conditions. Neither external chemical oxidants nor metal catalysts are required to facilitate the dehydrogenation processes. This reaction protocol provides an environmentally friendly way for the selective synthesis of benzofuroindolines. Various N -acetylindoles bearing different C-3 and C-2 substituents are suitable in this electrochemical transformation, furnishing corresponding benzofuroindolines in up to 99% yield. Electrochemical oxidation provides a green alternative to the use of hazardous chemical oxidants and forcing conditions. Here, the authors show the electrocatalytic cross-coupling of phenols and indoles to generate biologically relevant benzofuroindolines in high yields.
ISSN:2041-1723
2041-1723
DOI:10.1038/s41467-017-00873-1