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

Tan, Yichen and Muñoz-Molina, José María and Fu, Gregory C. and Peters, Jonas C. (2014) Oxygen nucleophiles as reaction partners in photoinduced, copper-catalyzed cross-couplings: O-arylations of phenols at room temperature. Chemical Science, 5 (7). pp. 2831-2835. ISSN 2041-6520. doi:10.1039/c4sc00368c.

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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.

Item Type:Article
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URLURL TypeDescription DOIArticle
Fu, Gregory C.0000-0002-0927-680X
Peters, Jonas C.0000-0002-6610-4414
Additional Information:© 2014 The Royal Society of Chemistry. Received 3rd February 2014; Accepted 17th April 2014. First published online 22 Apr 2014. This work was supported by the Gordon and Betty Moore Foundation (grant to J.C.P.) and the Council for International Exchange of Scholars (Fulbright Scholar award to J.M.M.-M.). We thank Daniel T. Ziegler for preliminary studies, Sidney E. Creutz for experimental assistance, and the reviewers for constructive comments.
Funding AgencyGrant Number
Gordon and Betty Moore FoundationUNSPECIFIED
Council for International Exchange of ScholarsUNSPECIFIED
Issue or Number:7
Record Number:CaltechAUTHORS:20140710-132652083
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Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:47147
Deposited By: Tony Diaz
Deposited On:10 Jul 2014 20:54
Last Modified:10 Nov 2021 17:35

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