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Palladium-Catalyzed Carbonylation of Aryl Tosylates and Mesylates
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Abstract
A general protocol for the palladium-catalyzed carbonylation of aryl tosylates and mesylates to form esters has been developed using a catalyst system derived from Pd(OAc)2 and the bulky, bidentate dcpp ligand. The system operates under mild conditions: atmospheric CO pressure and temperatures of 80−110 °C. A broad substrate scope has been demonstrated allowing carbonylation of electron-rich, electron-poor, and heterocyclic tosylates and mesylates, and the reaction shows wide functional group tolerance.
Citing Articles
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This article has been cited by 27 ACS Journal articles (5 most recent appear below).
Synthesis of Benzoylacetonitriles from Pd-Catalyzed Carbonylation of Aryl Iodides and Trimethylsilylacetonitrile
Ahbyeol Park and Sunwoo LeeOrganic Letters2012 Article ASAPSynthesis of Benzoylacetonitriles from Pd-Catalyzed Carbonylation of Aryl Iodides and Trimethylsilylacetonitrile
Ahbyeol Park and Sunwoo LeeOrganic Letters2012 Article ASAPPalladium-catalyzed carbonylation of aryl iodides and trimethylsilylacetonitrile to produce benzoylacetonitrile derivatives through a one-pot, three-component reaction is described. This preparation method provides good yields of the carbonylated products ...
Silacarboxylic Acids as Efficient Carbon Monoxide Releasing Molecules: Synthesis and Application in Palladium-Catalyzed Carbonylation Reactions
Stig D. Friis, Rolf H. Taaning, Anders T. Lindhardt, and Troels SkrydstrupJournal of the American Chemical Society2011 133 (45), 18114-18117Silacarboxylic Acids as Efficient Carbon Monoxide Releasing Molecules: Synthesis and Application in Palladium-Catalyzed Carbonylation Reactions
Stig D. Friis, Rolf H. Taaning, Anders T. Lindhardt, and Troels SkrydstrupJournal of the American Chemical Society2011 133 (45), 18114-18117Silacarboxylic acids have been demonstrated to be easy to handle, air-stable carbon monoxide precursors. Different silacarboxylic acids were synthesized from the corresponding chlorosilanes and carbon dioxide, and their decarbonylation, upon treatment ...
Ex Situ Generation of Stoichiometric and Substoichiometric 12CO and 13CO and Its Efficient Incorporation in Palladium Catalyzed Aminocarbonylations
Philippe Hermange, Anders T. Lindhardt, Rolf H. Taaning, Klaus Bjerglund, Daniel Lupp, and Troels SkrydstrupJournal of the American Chemical Society2011 133 (15), 6061-6071Ex Situ Generation of Stoichiometric and Substoichiometric 12CO and 13CO and Its Efficient Incorporation in Palladium Catalyzed Aminocarbonylations
Philippe Hermange, Anders T. Lindhardt, Rolf H. Taaning, Klaus Bjerglund, Daniel Lupp, and Troels SkrydstrupJournal of the American Chemical Society2011 133 (15), 6061-6071A new technique for the ex situ generation of carbon monoxide (CO) and its efficient incorporation in palladium catalyzed carbonylation reactions was achieved using a simple sealed two-chamber system. The ex situ generation of CO was derived by a ...
Palladium Catalyzed Alkoxy- and Aminocarbonylation of Vinyl Tosylates
Diana C. Reeves, Sonia Rodriguez, Heewon Lee, Nizar Haddad, Dhileepkumar Krishnamurthy, and Chris H. SenanayakeOrganic Letters2011 Article ASAPPalladium Catalyzed Alkoxy- and Aminocarbonylation of Vinyl Tosylates
Diana C. Reeves, Sonia Rodriguez, Heewon Lee, Nizar Haddad, Dhileepkumar Krishnamurthy, and Chris H. SenanayakeOrganic Letters2011 Article ASAPThe palladium catalyzed alkoxycarbonylation and aminocarbonylation of vinyl tosylates are described. A variety of ketone and aldehyde derived vinyl tosylates may be carbonylated in the presence of primary, secondary, and tertiary alcohols, or primary and ...
Carbonylative Heck Reactions Using CO Generated ex Situ in a Two-Chamber System
Philippe Hermange, Thomas M. Gøgsig, Anders T. Lindhardt, Rolf H. Taaning, and Troels SkrydstrupOrganic Letters2011 Article ASAPCarbonylative Heck Reactions Using CO Generated ex Situ in a Two-Chamber System
Philippe Hermange, Thomas M. Gøgsig, Anders T. Lindhardt, Rolf H. Taaning, and Troels SkrydstrupOrganic Letters2011 Article ASAPA carbonylative Heck reaction of aryl iodides and styrene derivatives employing a two-chamber system using a stable, crystalline, and nontransition metal based carbon monoxide source is reported. By applying near-stoichiometric amounts of the carbon ...
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History
- Published In Issue March 05, 2008
- Received January 2, 2008
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