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Aryl Dance Reaction of Arylheteroles

25 May 2022, Version 1
Working Paper
This content is an early or alternative research output and has not been peer-reviewed by Cambridge University Press at the time of posting.

Abstract

We have discovered a 1,2-migration (aryl dance reaction) of the aryl group on heteroles. AlCl3 can efficiently convert C3-arylheteroles to C2-arylheteroles. Depending on the electron density of the substrate, conversion from C2- to C3-arylheteroles was also possible with catalytic Zn(OTf)2. A one-pot aryl dance/acylation or bromination, and arylation/aryl dance was also demonstrated.

Keywords

dance reaction
arylheteroles
thiophene
indole
arylation

Supplementary materials

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Supplementary information
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For experimental procedures, spectroscopic data for compounds including 1H, 13C, and 19F NMR spectra
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Supplementary weblinks

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Yamaguchi Lab
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Junichiro Yamaguchi Lab webpage
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Now Published

Aryl Dance Reaction of Arylbenzoheteroles [opens in a new tab]
Hikaru Nakahara, Junichiro Yamaguchi journal article
Organic Letters , Volume 24, Issue 43
Online publication date: Oct 26, 2022

Version History

May 25, 2022 Version 1

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The content is available under CC BY NC 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2022-bl6rx
D O I: 10.26434/chemrxiv-2022-bl6rx [opens in a new tab]

Funding

Japan Society for the Promotion of Science
JP21H05213
Exploratory Research for Advanced Technology
JPMJER1901

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) declare that they have sought and gained approval from the relevant ethics committee/IRB for this research and its publication.

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