Combined Metalation-Palladium-Catalyzed Cross Coupling Strategies. A Formal Synthesis of the Marine Alkaloid Amphimedine

1995 ◽  
Vol 60 (2) ◽  
pp. 292-296 ◽  
Author(s):  
F. Guillier ◽  
F. Nivoliers ◽  
A. Godard ◽  
F. Marsais ◽  
G. Queguiner ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Formal Synthesis ◽  
Marine Alkaloid ◽  
Palladium Catalyzed ◽  
Coupling Strategies

ChemInform Abstract: Combined Metalation-Palladium-Catalyzed Cross Coupling Strategies. A Formal Synthesis of the Marine Alkaloid Amphimedine.

ChemInform ◽  
2010 ◽  
Vol 26 (30) ◽  
pp. no-no
Author(s):  
F. GUILLIER ◽  
F. NIVOLIERS ◽  
A. GODARD ◽  
F. MARSAIS ◽  
G. QUEGUINER ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Formal Synthesis ◽  
Marine Alkaloid ◽  
Palladium Catalyzed ◽  
Coupling Strategies

General Platform for the Conversion of Isoxazol-5-ones to 3,5-Disubstituted Isoxazoles via Nucleophilic Substitutions and Palladium Catalyzed Cross-Coupling Strategies

2019 ◽  
Vol 2019 (19) ◽  
pp. 3022-3034 ◽  
Author(s):  
Alessandra A. G. Fernandes ◽  
Amanda F. da Silva ◽  
Celso Y. Okada ◽  
Vitor Suzukawa ◽  
Rodrigo A. Cormanich ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Nucleophilic Substitutions ◽  
Palladium Catalyzed ◽  
Coupling Strategies

Efficient synthesis of 5-aryl-2-vinylfurans by palladium catalyzed cross-coupling strategies

1999 ◽  
Vol 40 (26) ◽  
pp. 4769-4773 ◽  
Author(s):  
Devan Balachari ◽  
Liam Quinn ◽  
George A. O'Doherty
Keyword(s):  
Cross Coupling ◽  
Efficient Synthesis ◽  
Palladium Catalyzed ◽  
Coupling Strategies

Suzuki–Miyaura cross-coupling for chemoproteomic applications

2020 ◽  
Author(s):  
Jian Cao ◽  
Ernest Armenta ◽  
Lisa Boatner ◽  
Heta Desai ◽  
Neil Chan ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Cross Coupling ◽  
Protein Profiling ◽  
Protein Labeling ◽  
Caspase 8 ◽  
Complex Cell ◽  
Bioorthogonal Chemistry ◽  
Reaction Conditions ◽  
Target Deconvolution ◽  
Palladium Catalyzed

Bioorthogonal chemistry is a mainstay of chemoproteomic sample preparation workflows. While numerous transformations are now available, chemoproteomic studies still rely overwhelmingly on copper-catalyzed azide –alkyne cycloaddition (CuAAC) or 'click' chemistry. Here we demonstrate that gel-based activity-based protein profiling (ABPP) and mass-spectrometry-based chemoproteomic profiling can be conducted using Suzuki–Miyaura cross-coupling. We identify reaction conditions that proceed in complex cell lysates and find that Suzuki –Miyaura cross-coupling and CuAAC yield comparable chemoproteomic coverage. Importantly, Suzuki–Miyaura is also compatible with chemoproteomic target deconvolution, as demonstrated using structurally matched probes tailored to react with the cysteine protease caspase-8. Uniquely enabled by the observed orthogonality of palladium-catalyzed cross-coupling and CuAAC, we combine both reactions to achieve dual protein labeling.

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