Selective Preparation of C 2v -Symmetric Hexaphenylbenzene Derivatives through Sequential Suzuki Coupling

Synlett ◽  
2018 ◽  
Vol 29 (12) ◽  
pp. 1597-1600 ◽  
Author(s):  
Tatsuo Kojima ◽  
Shuichi Hiraoka ◽  
Kazuho Ogata
Keyword(s):  
Cross Coupling ◽  
Suzuki Coupling ◽  
Nickel Catalysts ◽  
Phosphine Ligands ◽  
Reaction Conditions ◽  
Aryl Group ◽  
Chloro Group ◽  
Effective Reaction

We have developed effective reaction conditions for the ­Suzuki cross-coupling of chlorinated hexaphenylbenzene derivatives. A chloro group on a hexaphenylbenzene framework exhibits a low reactivity to Suzuki cross-coupling, and only nickel catalysts bearing alkyl-substituted phosphine ligands achieved the coupling. With this as a key step, we succeeded in the selective preparation of a C 2v -symmetric hexaphenylbenzene derivative containing two kinds of aryl group.

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.

scholarly journals Cross‐Coupling of Aryl/Alkenyl Pivalates with Organozinc Reagents through Nickel‐Catalyzed CO Bond Activation under Mild Reaction Conditions

2009 ◽  
Vol 48 (8) ◽  
pp. 1351-1351
Author(s):  
Bi‐Jie Li ◽  
Yi‐Zhou Li ◽  
Xing‐Yu Lu ◽  
Jia Liu ◽  
Bing‐Tao Guan ◽  
...  
Keyword(s):  
Bond Activation ◽  
Cross Coupling ◽  
Reaction Conditions ◽  
Organozinc Reagents

Comparison of the Suzuki cross-coupling reactions of 4,7-dichloroquinoline and 7-chloro-4-iodoquinoline with arylboronic acids using phosphine-free palladium catalysis in water

2004 ◽  
Vol 82 (2) ◽  
pp. 206-214 ◽  
Author(s):  
Richard W Friesen ◽  
Laird A Trimble
Keyword(s):  
Phenylboronic Acid ◽  
Palladium Catalysis ◽  
Suzuki Reaction ◽  
Tetrabutylammonium Bromide ◽  
Cross Coupling ◽  
Palladium Acetate ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
Arylboronic Acids ◽  
Cross Coupling Reactions

4,7-Dichloroquinoline (1a) and 7-chloro-4-iodoquinoline (1b) undergo Suzuki cross-coupling reactions with arylboronic acids catalyzed by phosphine-free palladium acetate in boiling water. Using phenylboronic acid (2), the reaction of 1a provides 7-chloro-4-phenylquinoline (3) (78%) together with diphenylquinoline (4) (12%), while 1b reacts in a much more regioselective fashion and provides 3 in 98% isolated yield. Although 1b undergoes a more regioselective Suzuki reaction than 1a, additional important observations are that the overall reaction of 1b with 2 is three times slower than 1a and that the reaction occurs in the absence of tetrabutylammonium bromide. Using optimized reaction conditions, a variety of aryl and vinylboronic acids undergo regioselective Suzuki cross-coupling with 1b to provide the products 7, 10, and 11 in good to excellent yield.Key words: palladium, cross-coupling, regioselectivity, quinolines, boronic acids.

scholarly journals Efficient in situ N-heterocyclic carbene palladium(ii) generated from Pd(OAc)2 catalysts for carbonylative Suzuki coupling reactions of arylboronic acids with 2-bromopyridine under inert conditions leading to unsymmetrical arylpyridine ketones: synthesis, characterization and cytotoxic activities

RSC Advances ◽  
2018 ◽  
Vol 8 (70) ◽  
pp. 40000-40015 ◽  
Author(s):  
Nedra Touj ◽  
Abdullah S. Al-Ayed ◽  
Mathieu Sauthier ◽  
Lamjed Mansour ◽  
Abdel Halim Harrath ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Suzuki Coupling ◽  
Boronic Acids ◽  
Cytotoxic Activities ◽  
Coupling Reactions ◽  
Component System ◽  
Arylboronic Acids ◽  
Cross Coupling Reaction

The in situ prepared four component system Pd(OAc)2, 1,3-dialkylbenzimidazolium halides 2a–i and 4a–i, K2CO3 under CO atmosphere catalyses carbonylative cross-coupling reaction of 2-bromopyridine with various boronic acids to yield unsymmetrical arylpyridine ketones.

Reaction de méthanation du gaz de synthèse: Influence de la température de calcination des catalyseurs à base de nickel

1993 ◽  
Vol 71 (1) ◽  
pp. 107-111
Author(s):  
M. Ghazi ◽  
J. Barrault
Keyword(s):  
Nickel Content ◽  
Great Part ◽  
Extreme Temperature ◽  
Nickel Catalysts ◽  
Economic Situation ◽  
Reaction Conditions ◽  
Methanation Reaction ◽  
Different Temperatures ◽  
Usual Process ◽  
Important Activity

Due to their important activity and selectivity, nickel catalysts are often used to realize the methanation reaction; however, the usual process based on these catalysts is not fitted for the present economic situation. To raise their stability, three catalysts with similar nickel content but calcinated at different temperatures have been studied for the reaction of methanation. The results obtained show that the catalyst calcinated at the highest temperature (973 K) shows the greatest promise because a great part of its activity and of its stability is preserved even when the reaction conditions are extreme (temperature of 773 K).

scholarly journals Synthesis of 9-arylalkynyl- and 9-aryl-substituted benzo[b]quinolizinium derivatives by Palladium-mediated cross-coupling reactions

2018 ◽  
Vol 14 ◽  
pp. 1871-1884 ◽  
Author(s):  
Siva Sankar Murthy Bandaru ◽  
Darinka Dzubiel ◽  
Heiko Ihmels ◽  
Mohebodin Karbasiyoun ◽  
Mohamed M A Mahmoud ◽  
...  
Keyword(s):  
Emission Intensity ◽  
Binding Constants ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Sonogashira Coupling ◽  
Reaction Conditions ◽  
Quadruplex Dna ◽  
Cross Coupling Reactions ◽  
Sonogashira Coupling Reaction

9-Arylbenzo[b]quinolizinium derivatives were prepared with base-free Suzuki–Miyaura coupling reactions between benzo[b]quinolizinium-9-trifluoroborate and selected benzenediazonium salts. In addition, the Sonogashira coupling reaction between 9-iodobenzo[b]quinolizinium and the arylalkyne derivatives yielded four novel 9-(arylethynyl)benzo[b]quinolizinium derivatives under relatively mild reaction conditions. The 9-(N,N-dimethylaminophenylethynyl)benzo[b]quinolizinium is only very weakly emitting, but the emission intensity increases by a factor >200 upon protonation, so that this derivative may operate as pH-sensitive light-up probe. Photometric and fluorimetric titrations of duplex and quadruplex DNA to 9-(arylethynyl)benzo[b]quinolizinium derivatives revealed a significant binding affinity of these compounds towards both DNA forms with binding constants ofKb= 0.2–2.2 × 105M−1.

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.

Aryl-Diadamantyl Phosphine Ligands in Palladium-Catalyzed Cross-Coupling Reactions: Synthesis, Structural Analysis, and Application

2020 ◽  
Vol 2020 (9) ◽  
pp. 1122-1128
Author(s):  
Ádám Sinai ◽  
Dániel Cs. Simkó ◽  
Fruzsina Szabó ◽  
Attila Paczal ◽  
Tamás Gáti ◽  
...  
Keyword(s):  
Structural Analysis ◽  
Cross Coupling ◽  
Phosphine Ligands ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed

scholarly journals Perfluorinated phosphine and hybrid P–O ligands for Pd catalysed C–C bond forming reactions in solution and on Teflon supports

RSC Advances ◽  
2019 ◽  
Vol 9 (50) ◽  
pp. 28936-28945
Author(s):  
Farzana Begum ◽  
Muhammad Ikram ◽  
Brendan Twamley ◽  
Robert J. Baker
Keyword(s):  
Cross Coupling ◽  
Phosphine Ligands ◽  
Coupling Reactions ◽  
Bond Forming ◽  
Cross Coupling Reactions ◽  
Bond Forming Reactions

Phosphine ligands containing a perfluorous ponytail can be sorbed onto Teflon tape and used as ligands for C–C cross coupling reactions with little leaching.

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