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Ring-Expansion and Desulfurisation of Thiophenes with an Aluminium(I) Reagent

15 September 2023, 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This content is an early or alternative research output and has not been peer-reviewed by Cambridge University Press at the time of posting.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

Reactions of thiophene, 2-methylthiophene, 2-methoxythiophene, 2,3-dimethylthiophene, and benzothiophene with the aluminium(I) complex [{(ArNCMe)2CH}Al] (Ar = 2,6-di-isopropylphenyl) are reported. In all cases, carbon–sulfur bond activation and ring-expansion of the heterocycle is observed. For thiophene, we identify a reaction network for desulfurisation that includes an unusual second carbon–sulfur bond activation step.

Keywords

Desulfurisation
Aluminium
Thiophene

Supplementary materials

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Supporting Information
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Experimental procedures, characterisation data, and computational details (PDF).
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xyz
Description
Coordinates from DFT calculations
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CIF
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.cif files for XRD data
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Version History

Sep 15, 2023 Version 1

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

DOI

10.26434/chemrxiv-2023-rd5jj
D O I: 10.26434/chemrxiv-2023-rd5jj [opens in a new tab]

Funding

Imperial College London
Presidents Scholarship to JM

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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