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Updated: Jun 11, 2025

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
Carbene transfer reactivity from a nickelacyclobutane
María L G Sansores-Paredes1, Martin Lutz2, Marc-Etienne Moret1
1Organic Chemistry and Catalysis, Institute for Sustainable and Circular Chemistry, Faculty of Science, Utrecht University, Universiteitsweg 99, 3584 CG, Utrecht, The Netherlands. m.moret@uu.nl.
Abstract:
A formal carbene-transfer reaction from an isolated nickelacyclobutane to an isocyanide to form a ketenimine is reported. DFT calculations support a stepwise 1,1-insertion/fragmentation pathway without a carbene intermediate. This unusual reactivity suggests a potential new role as "carbene reservoir" for nickelacyclobutanes, which are typically seen as intermediates in catalytic cyclopropanation.
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