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Updated: Jan 25, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
Carbene Formation and Transfer at a Dinickel Active Site
Arnab K Maity1, Mathias Zeller1, Christopher Uyeda1
1Department of Chemistry, Purdue University, West Lafayette, Indiana 47907, United States.
Abstract:
The synthesis and reactivity of a dinickel bridging carbene is described. The previously reported [ NDI]Ni2(C6H6) complex (NDI = naphthyridine-diimine) reacts with Ph2CN2 to generate a metastable diazoalkane adduct, which eliminates N2 at 60 °C to yield a paramagnetic Ni2(μ-CPh2) complex. The Ni2(μ-CPh2) complex undergoes carbene transfer to t-BuNC via an initial isonitrile adduct, which, upon heating, releases free t-BuNCCPh2. Based on this sequence of stoichiometric reactions, a catalytic carbene transfer reaction is demonstrated.
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