Issue 11, 2022
From the journal:

Chemical Science

Intramolecular photochemical [2 + 1]-cycloadditions of nucleophilic siloxy carbenes†

Amanda Bunyamin,a   Carol Hua, ORCID logo ab   Anastasios Polyzos ORCID logo ac  and  Daniel L. Priebbenow ORCID logo *ad  

* Corresponding authors

a School of Chemistry, University of Melbourne, Parkville, Victoria, 3010 Australia
E-mail: daniel.priebbenow@unimelb.edu.au

b School of Life and Environmental Sciences, Deakin University, Waurn Ponds, Victoria, 3216 Australia

c CSIRO Manufacturing, Clayton, Victoria, 3168 Australia

d Department of Medicinal Chemistry, Monash Institute of Pharmaceutical Science, Monash University, Parkville, Victoria, 3052 Australia

Abstract

Visible light induced singlet nucleophilic carbenes 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 process requires only visible light irradiation to proceed, circumventing the use of exogenous (photo)catalysts, sensitisers or additives and showcases a vastly underexplored mode of reactivity for nucleophilic carbenes in chemical synthesis. The discovery of additional transformations including a cyclopropanation/retro-Michael/Michael cascade process to afford chromanones and a photochemical C–H insertion reaction are also described.

Graphical abstract: Intramolecular photochemical [2 + 1]-cycloadditions of nucleophilic siloxy carbenes

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Article information

DOI
https://doi.org/10.1039/D2SC00203E
Article type
Edge Article
Submitted
12 Jan 2022
Accepted
24 Feb 2022
First published
25 Feb 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2022,13, 3273-3280

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Intramolecular photochemical [2 + 1]-cycloadditions of nucleophilic siloxy carbenes

A. Bunyamin, C. Hua, A. Polyzos and D. L. Priebbenow, Chem. Sci., 2022, 13, 3273 DOI: 10.1039/D2SC00203E

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