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Non-innocent Role of the Halide Ligand in the Copper-Catalyzed Olefin Aziridination Reaction. | LitMetric

Non-innocent Role of the Halide Ligand in the Copper-Catalyzed Olefin Aziridination Reaction.

ACS Catal

Laboratorio de Catálisis Homogénea, Unidad Asociada al CSIC, CIQSO-Centro de Investigación en Química Sostenible and Departamento de Química, Universidad de Huelva, 21007 Huelva, Spain.

Published: January 2023

In the context of copper-catalyzed nitrene transfer to olefins, many systems operate upon mixing a CuX salt (X = halide, OTf) and a polydentate N-based ligand, assuming that the X ligand is displaced from the coordination sphere toward a counterion position. Herein, we demonstrated that such general assumption should be in doubt since studies carried out with the well-defined copper(I) complexes (TTM)CuCl and [(TTM)Cu(NCMe)]PF (TTM = tris(triazolyl)methane ligand) demonstrate a dual behavior from a catalytic and mechanistic point of view that exclusively depends on the presence or absence of the chloride ligand bonded to the metal center. When coordinated, the turnover-limiting step corresponds to the formation of the carbon-nitrene bond, whereas in its absence, the highest barrier corresponds to the formation of the copper-nitrene intermediate.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10552652PMC
http://dx.doi.org/10.1021/acscatal.2c05069DOI Listing

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