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Synthesis of Benzenes from Pyridines via N to C switch

06 February 2024, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

The transformation of pyridines into benzene derivatives is described, using a one-pot ANRORC process with soft nucleophiles such as malonate. Triflic anhydride activates the pyridine to ANRORC synthesis of a carbocyclic β-aminoester intermediate, which aromatizes on heating. The reaction has been exemplified with a room temperature protocol, along with direct syntheses of biologi-cally active, tertiary-alkylated and isotopically-labelled benzoates.

Keywords

Pyridine
Skeletal-editing
ANRORC

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Version History

Feb 06, 2024 Version 1

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

DOI

10.26434/chemrxiv-2024-tsjsm
D O I: 10.26434/chemrxiv-2024-tsjsm [opens in a new tab]

Funding

EPSRC Centre for Doctoral Training in Integrated Catalysis
EP/023755/1

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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