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Journal Article

alpha-Radical Phosphines: Synthesis, Structure, and Reactivity


Bill,  Eckhard
Research Department Neese, Max Planck Institute for Chemical Energy Conversion, Max Planck Society;

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Gu, L., Zheng, Y., Haldon, E., Goddard, R., Bill, E., Thiel, W., et al. (2017). alpha-Radical Phosphines: Synthesis, Structure, and Reactivity. Angewandte Chemie, International Edition in English, 56(30), 8790-8794. doi:10.1002/anie.201704185.

Cite as: https://hdl.handle.net/21.11116/0000-0007-1611-D
A series of phosphines featuring a persistent radical were synthesized in two steps by condensation of dialkyl-/diarylchlorophosphines with stable cyclic (alkyl)(amino)carbenes (cAACs) followed by one-electron reduction of the corresponding cationic intermediates. Structural, spectroscopic, and computational data indicate that the spin density in these phosphines is mainly localized on the original carbene carbon from the cAAC fragment; thus, it remains in the a-position with respect to the central phosphorus atom. The potential of these alpha-radical phosphines to serve as spin-labeled ligands is demonstrated through the preparation of several Au-I derivatives, which were also structurally characterized by single-crystal X-ray diffraction.