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Photoinduced Ullmann C–N Coupling: Demonstrating the Viability of a Radical Pathway

Creutz, Sidney E. and Lotito, Kenneth J. and Fu, Gregory C. and Peters, Jonas C. (2012) Photoinduced Ullmann C–N Coupling: Demonstrating the Viability of a Radical Pathway. Science, 338 (6107). pp. 647-651. ISSN 0036-8075. doi:10.1126/science.1226458.

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Carbon–nitrogen (C–N) bond-forming reactions of amines with aryl halides to generate arylamines (anilines), mediated by a stoichiometric copper reagent at elevated temperature (>180°C), were first described by Ullmann in 1903. In the intervening century, this and related C–N bond-forming processes have emerged as powerful tools for organic synthesis. Here, we report that Ullmann C–N coupling can be photoinduced by using a stoichiometric or a catalytic amount of copper, which enables the reaction to proceed under unusually mild conditions (room temperature or even –40°C). An array of data are consistent with a single-electron transfer mechanism, representing the most substantial experimental support to date for the viability of this pathway for Ullmann C–N couplings.

Item Type:Article
Related URLs:
URLURL TypeDescription DOIArticle
Fu, Gregory C.0000-0002-0927-680X
Peters, Jonas C.0000-0002-6610-4414
Additional Information:© 2012 American Association for the Advancement of Science. Received 22 June 2012; accepted 10 September 2012. This work was supported by the National Science Foundation (graduate research fellowships for S.E.C. and K.J.L.) and by the Gordon and Betty Moore Foundation. Metrical parameters for the structure of copper complex 1 are available free of charge from the Cambridge Crystallographic Data Centre under reference CCDC-896019.
Funding AgencyGrant Number
NSF Graduate Research FellowshipUNSPECIFIED
Gordon and Betty Moore FoundationUNSPECIFIED
Issue or Number:6107
Record Number:CaltechAUTHORS:20121127-143024844
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Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:35683
Deposited On:28 Nov 2012 00:12
Last Modified:09 Nov 2021 23:17

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