Issue 79, 2023

Photogenerated donor–donor diazo compounds enable facile access to spirocyclopropanes

Abstract

Prompted by the increasing interest in strained hydrocarbons as potential drug candidates, we developed a simple and efficient photochemical protocol for (spiro)cyclopropanes from bench stable tosylhydrazones and electron poor olefins. This two-step one-pot transformation proceeds by (3+2)-cycloaddition of in situ formed donor–donor diazo compounds, followed by nitrogen extrusion of the Δ1-pyrazoline intermediates. Notably, kinetic analysis enabled the isolation of intermediary spiro-heterocycles.

Graphical abstract: Photogenerated donor–donor diazo compounds enable facile access to spirocyclopropanes

Supplementary files

Article information

Article type
Communication
Submitted
25 Jul 2023
Accepted
08 Sep 2023
First published
11 Sep 2023

Chem. Commun., 2023,59, 11835-11838

Photogenerated donor–donor diazo compounds enable facile access to spirocyclopropanes

V. George and B. König, Chem. Commun., 2023, 59, 11835 DOI: 10.1039/D3CC03581F

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