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Photochemical [2+1]-Cycloadditions of Nucleophilic Carbenes

29 November 2021, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Visible light induced singlet nucleophilic carbene intermediates undergo rapid [2+1]-cycloaddition with tethered olefins to afford unique bicyclo[3.1.0]hexane and bicyclo[4.1.0]heptane scaffolds. This cyclopropanation proceeds using only visible light irradiation, circumventing the use of exogenous (photo)catalysts or sensitisers and showcases an underexplored mode of reactivity for nucleophilic carbenes in chemical synthesis. The discovery of additional transformations including a cyclopropanation/retro-Michael/Michael cascade reaction to afford chromanone derivatives are also described.

Keywords

carbene
cycloaddition
photochemistry

Supplementary materials

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Description
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Graphical Abstract
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Graphical Abstract
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Title
Photochemical [2+1]-Cycloadditions of Nucleophilic Carbenes - Supporting Information
Description
Photochemical [2+1]-Cycloadditions of Nucleophilic Carbenes - Supporting Information
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Now Published

Intramolecular photochemical [2 + 1]-cycloadditions of nucleophilic siloxy carbenes [opens in a new tab]
Amanda Bunyamin, Carol Hua, Anastasios Polyzos, Daniel L. Priebbenow journal article
Chemical Science , Volume 13, Issue 11
Online publication date: 2022

Version History

Nov 29, 2021 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-2021-0rfst
D O I: 10.26434/chemrxiv-2021-0rfst [opens in a new tab]

Funding

Australian Research Council
DE200100949

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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