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Issue 20, 2019
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Catalytic reduction of aryl trialkylammonium salts to aryl silanes and arenes

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Abstract

A new approach for the reduction of aryl ammonium salts to arenes or aryl silanes using nickel catalysis is reported. This method displays excellent ligand-controlled selectivity based on the N-heterocyclic carbene (NHC) ligand employed. Utilizing a large NHC in non-polar solvents generates aryl silanes, while small NHCs in polar solvents promote reduction to arenes. Several classes of aryl silanes can be accessed from simple aniline building blocks, including those useful for cross-couplings, oxidations, and halogenations. The reaction conditions are mild, functional group tolerant, and provide efficient access to a variety of benzene derivatives.

Graphical abstract: Catalytic reduction of aryl trialkylammonium salts to aryl silanes and arenes

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Publication details

The article was received on 04 Mar 2019, accepted on 22 Apr 2019 and first published on 26 Apr 2019


Article type: Edge Article
DOI: 10.1039/C9SC01083A
Chem. Sci., 2019,10, 5338-5344
  • Open access: Creative Commons BY-NC license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    Catalytic reduction of aryl trialkylammonium salts to aryl silanes and arenes

    Alexander W. Rand and J. Montgomery, Chem. Sci., 2019, 10, 5338
    DOI: 10.1039/C9SC01083A

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