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Issue 7, 2014
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Oxygen nucleophiles as reaction partners in photoinduced, copper-catalyzed cross-couplings: O-arylations of phenols at room temperature

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Abstract

Most copper-catalyzed cross-couplings require an elevated reaction temperature. Recently, a photoinduced variant has been developed that enables C–X bond-forming reactions of certain nitrogen and sulfur nucleophiles to proceed under unusually mild conditions (−40 °C to room temperature). In view of the importance of carbon–oxygen bond construction in organic chemistry, the expansion of this photochemical approach to oxygen nucleophiles is an important objective. In this report, we establish that, in the presence of light and an inexpensive copper pre-catalyst (CuI), a wide array of phenols and aryl iodides can be coupled to generate diaryl ethers under mild conditions (room temperature) in the presence of a variety of functional groups. Our studies indicate that a Cu(I)–phenoxide complex is a viable intermediate in photoinduced C–O bond-formation.

Graphical abstract: Oxygen nucleophiles as reaction partners in photoinduced, copper-catalyzed cross-couplings: O-arylations of phenols at room temperature

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Publication details

The article was received on 03 Feb 2014, accepted on 17 Apr 2014 and first published on 22 Apr 2014


Article type: Edge Article
DOI: 10.1039/C4SC00368C
Citation: Chem. Sci., 2014,5, 2831-2835
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    Oxygen nucleophiles as reaction partners in photoinduced, copper-catalyzed cross-couplings: O-arylations of phenols at room temperature

    Y. Tan, J. M. Muñoz-Molina, G. C. Fu and J. C. Peters, Chem. Sci., 2014, 5, 2831
    DOI: 10.1039/C4SC00368C

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