Thomas M. Gøgsig
Aarhus University
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Publication
Featured researches published by Thomas M. Gøgsig.
Journal of Organic Chemistry | 2008
Thomas M. Gøgsig; Lina Sveidal Søbjerg; Anders T. Lindhardt; Kim L. Jensen; Troels Skrydstrup
General reaction conditions were developed for the Pd(0)-catalyzed Suzuki-Miyaura coupling reaction of aryl boronic acids with a simple electrophilic vinylation reagent, vinyl tosylate, providing access to styrene derivatives in good yields. The easily accessible vinyl tosylate represents a stable and less toxic alternative to the vinyl halides and the triflate/nonaflate derivatives. Furthermore, this methodology was expanded to provide a facile and straightforward approach for the introduction of a gem-difluorovinyl substituent onto an aromatic ring using the similar and also readily available 2,2-difluorovinyl tosylate as the electrophilic complement.
Organic Letters | 2011
Philippe Hermange; Thomas M. Gøgsig; Anders T. Lindhardt; Rolf H. Taaning; Troels Skrydstrup
A 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 monoxide precursor, an effective exploitation of the hazardous CO gas is obtained affording chalcone derivatives in good yields. Application to isotope labeling, incorporating (13)CO, was further established.
Organic Letters | 2009
Thomas M. Gøgsig; Anders T. Lindhardt; Troels Skrydstrup
Employment of heteroaromatic tosylates and phosphates as suitable electrophiles in iron-catalyzed cross-coupling reactions with alkyl Grignard reagents is reported. These reactions are performed at low temperature allowing good functional group tolerance and full conversion is achieved within minutes. In addition, an aryl-aryl cross-coupling utilizing a heteroaryl sulfamate electrophile is reported.
Journal of Organic Chemistry | 2009
Delphine Gauthier; Stephan Beckendorf; Thomas M. Gøgsig; Anders T. Lindhardt; Troels Skrydstrup
Kumada-Corriu cross-couplings of nonactivated cyclic and acyclic vinyl phosphates with aryl magnesium reagents afforded a series of 1,1-disubtituted alkenes in good yields for most cases when the reactions were performed at room temperature with the simple palladium salt, PdCl(2), without the presence of phosphine ligands.
Organic Letters | 2011
Dennis U. Nielsen; Rolf H. Taaning; Anders T. Lindhardt; Thomas M. Gøgsig; Troels Skrydstrup
A simple protocol is reported for the preparation of primary aryl amides under Pd-catalyzed carbonylation chemistry applying a two-chamber system with crystalline and nontransition metal based sources of carbon monoxide and ammonia. The method is suitable for the synthesis of a number of primary amides with good functional group tolerance. Incorporation of (13)CO into the primary amide group was also found to be effective making this approach useful for accessing carbon isotope labeled derivatives.
Chemistry: A European Journal | 2009
Thomas M. Gøgsig; Anders T. Lindhardt; Mouloud Dekhane; Julie Grouleff; Troels Skrydstrup
Heteroaromatic 2-pyridyl tosylates were successfully applied as electrophiles in palladium(0)-catalyzed Mizoroki-Heck-coupling reactions to electron-rich olefins with complete alpha-regioselectivity. This protocol represents a general strategy for the application of pyridyl tosylates and mesylates in the Mizoroki-Heck coupling. The catalytic system also proved adaptable to changes in the heteroaromatic core as well as large-scale applications. Finally, the synthetic utility of the functionalized alpha-heteroarylvinyl amides was established providing straightforward access to highly functionalized heteroaromatic compounds including chiral benzylic amide derivatives.
Organic Letters | 2012
Zhuo Xin; Thomas M. Gøgsig; Anders T. Lindhardt; Troels Skrydstrup
The palladium-catalyzed alkoxycarbonylation of aryl bromides is described for the efficient preparation of tertiary esters. The protocol proved compatible with a wide variety of functionalized (hetero)aromatic bromides, as well as several different sterically hindered tertiary alcohols, affording the alkoxycarbonylated products in high yields. Finally, the formation of aromatic trityl esters is discussed.
Organic Letters | 2012
Thomas M. Gøgsig; Dennis U. Nielsen; Anders T. Lindhardt; Troels Skrydstrup
The direct carbonylative palladium catalyzed synthesis of monoprotected 1,3-ketoaldehydes is reported starting from aryl iodides applying near stoichiometric amounts of carbon monoxide. Besides representing platforms for a variety of heterocyclic structures, these motives serve as viable precursors for the highly relevant aryl methyl ketones. The presented strategy can also be adapted for the facile and efficient incorporation of (13)C-labeled carbon monoxide.
Chemical Communications | 2006
Anders L. Hansen; Jean-Philippe Ebran; Thomas M. Gøgsig; Troels Skrydstrup
A combination of Ni(COD)(2) and PCy(3) promotes effectively the Suzuki-Miyaura cross coupling of 1-arylalkenyl phosphates with aryl boronic acids with yields attaining 99%.
Journal of Organic Chemistry | 2009
Anders T. Lindhardt; Thomas M. Gøgsig; Troels Skrydstrup
We report an initial investigation with the goal of determining the factors that control the 1,2-migration in the Negishi cross-coupling, which is promoted by palladium catalyst systems generated with JosiPhos ligands. Several of the factors that were demonstrated to be important for the 1,2-migration include (1) the nucleophilicity of the organometallic reagent, which possibly influences the transmetalation step in direct competition with the intermediate beta-hydride elimination of the alkenyl Pd(II) species; (2) the structural features of the vinyl tosylates and phosphates, in which substrates possessing a bulky C1 substituent displayed highest propensity for undergoing the 1,2-migration under the coupling reaction conditions; and (3) the structure of the JosiPhos ligand, where both the sterical bulk and choice of substituents on the ferrocenyl phosphino group greatly influence the catalytic activity of the palladium complex and its capacity to facilitate the 1,2-migration.