Sequential Reactions of Trimethylstannyl Anions with Vinyl Chlorides and Dichlorides by the SRN1 Mechanism Followed by Palladium-Catalyzed Cross-Coupling Processes

2004 ◽  
Vol 69 (19) ◽  
pp. 6427-6432 ◽  
Author(s):  
Eduardo F. Córsico ◽  
Roberto A. Rossi
Keyword(s):  
Cross Coupling ◽  
Palladium Catalyzed ◽  
Coupling Processes ◽  
Sequential Reactions

Additive effects on palladium-catalyzed deprotonative-cross-coupling processes (DCCP) of sp3C–H bonds in diarylmethanes

2013 ◽  
Vol 4 (2) ◽  
pp. 849-857 ◽  
Author(s):  
Ana Bellomo ◽  
Jiadi Zhang ◽  
Nisalak Trongsiriwat ◽  
Patrick J. Walsh
Keyword(s):  
Cross Coupling ◽  
Additive Effects ◽  
Palladium Catalyzed ◽  
Coupling Processes

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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