Palladium-catalyzed denitrogenative cross-coupling of aryl halides with arylhydrazines under mild reaction conditions

2021 ◽  
Author(s):  
Manjunatha Kempasiddaiah ◽  
Vishal Kandathil ◽  
Ramesh B. Dateer ◽  
B. S. Sasidhar ◽  
Shivaputra A. Patil ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Aryl Halides ◽  
Reaction Conditions ◽  
Palladium Catalyzed

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.

C(sp3)–H activation-enabled cross-coupling of two aryl halides: an approach to 9,10-dihydrophenanthrenes

2020 ◽  
Vol 56 (74) ◽  
pp. 10942-10945
Author(s):  
Yichao Gu ◽  
Xueliang Sun ◽  
Bin Wan ◽  
Zhuoer Lu ◽  
Yanghui Zhang
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Innovative Method ◽  
Cross Coupling Reaction ◽  
Chlorobenzoic Acids ◽  
Palladium Catalyzed

A palladium-catalyzed cross-coupling reaction of aryl halides with 2-chlorobenzoic acids has been developed through C(sp3)–H activation, which provides an innovative method for the synthesis of 9,10-dihydrophenanthren.

An active ferrocenyl triarylphosphine for palladium-catalyzed Suzuki–Miyaura cross-coupling of aryl halides

2004 ◽  
pp. 2336-2337 ◽  
Author(s):  
Fuk Yee Kwong ◽  
Kin Shing Chan ◽  
Chi Hung Yeung ◽  
Albert S. C. Chan
Keyword(s):  
Cross Coupling ◽  
Aryl Halides ◽  
Palladium Catalyzed

scholarly journals Synthesis of 2-Alkenyl-Tethered Anilines

Synthesis ◽  
2017 ◽  
Vol 49 (13) ◽  
pp. 2873-2888 ◽  
Author(s):  
Scott Denmark ◽  
Hyung Chi
Keyword(s):  
Lewis Acid ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Cope Rearrangement ◽  
The Third ◽  
Cross Metathesis ◽  
Direct Cross ◽  
Palladium Catalyzed

Three general routes for the synthesis of (E)-2-alkenyl-tethered anilines have been developed. The first route involves a 3-aza-Cope rearrangement of N-allylic anilines in the presence of a Lewis acid. The requisite N-allylic anilines were prepared by the addition of vinylmagnesium reagents to the corresponding aldimines. The second route details a direct cross-metathesis of 2-allylic or 2-homoallylic anilines with styrenes. The third route involves a palladium-catalyzed C–N cross-coupling of aryl halides. Taken together, these three strategies allowed access to the requisite aniline substrates with pendant alkenes at the 2-position with excellent trans selectivities.

Stereodivergent Hydrosilylation, Hydrostannylation, and Hydrogermylation of α-Trifluoromethylated Alkynes and Their Synthetic Applications

Synthesis ◽  
2016 ◽  
Vol 48 (19) ◽  
pp. 3317-3330 ◽  
Author(s):  
Cédric Tresse ◽  
Stéphane Schweizer ◽  
Philippe Bisseret ◽  
Jacques Lalevée ◽  
Gwilherm Evano ◽  
...  
Keyword(s):  
Functional Group ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed

Stereoselective hydrometalation reactions of aryl- and alkyl-substituted trifluoromethylated alkynes with triethylsilane, tributylstannane, and triphenylgermane have been investigated. (E)-α-CF3-Vinylsilanes, -stannanes, and -germanes were obtained under palladium-catalyzed conditions whereas the corresponding (Z)-α-CF3-vinylgermanes were obtained under radical conditions. These reactions proceed in good to excellent yields and possess a broad functional group tolerance. Applications of the (Z)- and (E)-α-CF3-vinylgermanes in palladium-catalyzed cross-coupling reactions with aryl halides having diverse electronic requirements were also investigated. The corresponding (Z)- and (E)-α-CF3-styrenes were obtained as single isomers, thus demonstrating the utility of these versatile synthons for the synthesis of stereodefined trifluoromethylated alkenes.

Regiospecific Palladium-Catalyzed Cross-Coupling Reactions Using the Operational Equivalent of 1,3-Dilithiopropyne

Synthesis ◽  
2020 ◽  
Vol 52 (16) ◽  
pp. 2387-2394 ◽  
Author(s):  
Jorge A. Cabezas ◽  
Natasha Ferllini
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Terminal Alkyne ◽  
Copper Iodide ◽  
Reaction Conditions ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
High Yields

A regiospecific palladium-catalyzed cross-coupling reaction using the operational equivalent of the dianion 1,3-dilithiopropyne, with aromatic iodides is reported. This reaction gives high yields of 1-propyn-1-yl-benzenes and 2-(propyn-1-yl)thiophenes in the presence of catalytic amounts of palladium(0) or (II) and stoichiometric amounts of copper iodide. No terminal alkyne or allene isomers were detected. Reaction conditions were very mild and several functional groups were tolerated.

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