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Synthesis of Benzofuropyridines and Dibenzofurans by a Metalation/Negishi Cross-Coupling/SNAr Reaction Sequence

20 July 2022, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

An efficient methodology for the synthesis of benzofuropyridines and dibenzofurans from fluoropyridines or fluoroarenes and 2-bromophenyl acetates is reported. This streamlined one-pot procedure consists of a four-step directed ortho-lithiation, zincation, Negishi cross-coupling, and intramolecular nucleophilic substitution, allowing for the facile assembly of a diverse set of fused benzofuro heterocycles.

Keywords

Benzofuropyridines
Dibenzofurans
Heterocycles
Directed lithiation
Negishi cross-coupling
SNAr

Supplementary materials

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Supporting Information
Description
The Supporting Information for this article contain experimental procedures and characterisation data for all new compounds, copies of 1H, 13C and 19F NMR spectra as well as crystallographic data.
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Now Published

Synthesis of Benzofuropyridines and Dibenzofurans by a Metalation/Negishi Cross-Coupling/SNAr Reaction Sequence [opens in a new tab]
Guy J. Clarkson, Stefan Roesner journal article
The Journal of Organic Chemistry
Online publication date: Dec 09, 2022

Version History

Jul 20, 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-2022-63g8k
D O I: 10.26434/chemrxiv-2022-63g8k [opens in a new tab]

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) have declared ethics committee/IRB approval is not relevant to this content

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