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Platinum-catalyzed Isomerization of Cyclopropenes to 1,3-Dienes

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

Abstract

Herein we report a platinum-catalyzed isomerization of cyclopropenes to 1,3-dienes. Diverse dienylated alcohols were ob-tained in 42-98% yield. The synthetic potential of the products was demonstrated by their use in Diels-Alder cycloadditions with various dienophiles. Isotope labelling studies provide strong support for a mechanism involving pericyclic [1,5]-σ-bond rearrangement of a vinyl platinum carbene intermediate.

Keywords

cyclopropenes
Platinum catalysis
isomerization
dienes
carbenes

Supplementary materials

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Description
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Supporting Information
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Experimental procedures, optimization data, spectra (PDF)
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Version History

May 14, 2024 Version 1

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

DOI

10.26434/chemrxiv-2024-ckv1v
D O I: 10.26434/chemrxiv-2024-ckv1v [opens in a new tab]

Funding

Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung
200020_212129

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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