Silver-Catalyzed Late-Stage Fluorination
- 9 August 2010
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 132 (34), 12150-12154
- https://doi.org/10.1021/ja105834t
Abstract
Carbon−fluorine bond formation by transition metal catalysis is difficult, and only a few methods for the synthesis of aryl fluorides have been developed. All reported transition-metal-catalyzed fluorination reactions for the synthesis of functionalized arenes are based on palladium. Here we present silver catalysis for carbon−fluorine bond formation. Our report is the first example of the use of the transition metal silver to form carbon−heteroatom bonds by cross-coupling catalysis. The functional group tolerance and substrate scope presented here have not been demonstrated for any other fluorination reaction to date.This publication has 43 references indexed in Scilit:
- Carbon-Fluorine Bond Formation for the Synthesis of Aryl FluoridesSynthesis, 2010
- Mechanism of C−F Reductive Elimination from Palladium(IV) FluoridesJournal of the American Chemical Society, 2010
- Bimetallic Palladium Catalysis: Direct Observation of Pd(III)−Pd(III) IntermediatesJournal of the American Chemical Society, 2009
- Formation of ArF from LPdAr(F): Catalytic Conversion of Aryl Triflates to Aryl FluoridesScience, 2009
- Regio- and Stereoselective Synthesis of Fluoroalkenes by Directed Au(I) CatalysisOrganic Letters, 2009
- Synthesis and Reactivity of a Mono-σ-Aryl Palladium(IV) Fluoride ComplexJournal of the American Chemical Society, 2009
- Carbon–heteroatom bond formation catalysed by organometallic complexesNature, 2008
- Elemental fluorine in organic chemistry (1997–2006)Journal of Fluorine Chemistry, 2007
- Über aromatische Fluorverbindungen, I.: Ein neues Verfahren zu ihrer DarstellungBerichte der deutschen chemischen Gesellschaft (A and B Series), 1927
- Gemischte Blei‐ und Zinn‐aryle und ‐aryl‐alkyle und ihre Verwendung zur Darstellung von Silber‐organoverbindungen, zugleich Beispiele für den Einfluß des Symmetriegrades auf die Eigenschaften chemischer VerbindungenBerichte der deutschen chemischen Gesellschaft (A and B Series), 1919