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Transition-Metal-Free Direct Arylation: Synthesis of Halogenated 2-Amino-2′-hydroxy-1,1′-biaryls and Mechanism by DFT Calculations

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    Transition-Metal-Free Direct Arylation: Synthesis of Halogenated 2-Amino-2′-hydroxy-1,1′-biaryls and Mechanism by DFT Calculations
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    † Division of Chemistry, Department of Biochemistry, UT Southwestern Medical Center, 5323 Harry Hines Boulevard, Dallas, Texas 75390, United States
    ‡ Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602, United States
    § Center for Nanostructured Materials, The University of Texas at Arlington, Arlington, Texas 76019, United States
    [email protected]
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    Cite this: J. Am. Chem. Soc. 2013, 135, 19, 7086–7089
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    https://doi.org/10.1021/ja400897u
    Published March 4, 2013
    Copyright © 2013 American Chemical Society
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    Abstract

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    A transition-metal-free, regioselective direct aryl–aryl bond-forming process for the synthesis of halogenated 2-amino-2′-hydroxy-1,1′-biaryls that are currently either inaccessible or challenging to prepare using conventional methods is disclosed. The addition of ArMgX to an o-halonitrobenzene at low temperature generates a transient N,O-biarylhydroxylamine that rapidly undergoes either [3,3]- or [5,5]-sigmatropic rearrangement in one-pot to form a 2-amino-2′-hydroxy-1,1′-biaryl or 1-amino-1′-hydroxy-4,4′-biaryl, respectively. The periselectivity is controlled by the choice of solvent and temperature. This direct arylation process is also readily scalable (1–10 mmol). DFT calculations suggest that from the N,O-biarylhydroxylamine intermediate there is a low-energy stepwise pathway that involves initial Mg-mediated N–O bond cleavage followed by pathway branching toward either [3,3]- or [5,5]-rearrangement products via C–C bond formation and rearomatization.

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    Experimental and computational details, characterization data, crystallographic data (CIF), and complete ref 18a. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Cite this: J. Am. Chem. Soc. 2013, 135, 19, 7086–7089
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