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Journal Article

Thorpe-Ingold Effect in Branch-Selective Alkylation of Unactivated Aryl Fluorides

MPS-Authors
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O'Neill,  Matthew J.
Research Group Cornellà, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Riesebeck,  Tim
Research Group Cornellà, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons207433

Cornella,  Josep
Research Group Cornellà, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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anie201804479-sup-0001-misc_information.pdf
(Supplementary material), 6MB

Citation

O'Neill, M. J., Riesebeck, T., & Cornella, J. (2018). Thorpe-Ingold Effect in Branch-Selective Alkylation of Unactivated Aryl Fluorides. Angewandte Chemie, International Edition, 57(29), 9103-9107. doi:10.1002/anie.201804479.


Cite as: https://hdl.handle.net/21.11116/0000-0001-AF4C-6
Abstract
Presented herein is a general protocol for the alkylation of simple aryl fluorides with unbiased secondary Grignard reagents by means of nickel catalysis. This study revealed a general Thorpe–Ingold effect in the ligand backbone which confers a high degree of selectivity for the secondary carbon center in the C−C coupling event. This protocol is characterized by mild reaction conditions, robustness, and simplicity. Both electron‐rich and electron‐deficient aryl fluorides are suitable candidates in this transformation. Equally amenable are a variety of heterocycles, permitting the coupling without over alkylation at the electrophilic sites.