Biphasic Aqueous Reaction Conditions for Process-Friendly Palladium-Catalyzed C–N Cross-Coupling of Aryl Amines

2019 ◽  
Vol 23 (8) ◽  
pp. 1752-1757 ◽  
Author(s):  
Subhash Pithani ◽  
Marcus Malmgren ◽  
Carl-Johan Aurell ◽  
Grigorios Nikitidis ◽  
Stig D. Friis
Keyword(s):  
Cross Coupling ◽  
Reaction Conditions ◽  
Palladium Catalyzed ◽  
Aryl Amines

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.

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.

Palladium-Catalyzed C–P Cross-Coupling between (Het)aryl Halides and Secondary Phosphine Oxides

Synthesis ◽  
2019 ◽  
Vol 51 (11) ◽  
pp. 2379-2386 ◽  
Author(s):  
Gladis Zakirova ◽  
Dmitrii Mladentsev ◽  
Nataliya Borisova
Keyword(s):  
Electronic Properties ◽  
Heterocyclic Compounds ◽  
Cross Coupling ◽  
Secondary Phosphine ◽  
Phosphine Oxides ◽  
Tertiary Phosphine ◽  
Reaction Conditions ◽  
Efficient Procedure ◽  
Palladium Catalyzed ◽  
Tertiary Alkyl

An efficient procedure for C–P bond formation via the palladium-catalyzed [Pd(OAc)2/dppf/Cs2CO3] reaction between dichloroheterocycles and secondary phosphine oxides was developed. The steric and electronic properties of substituents were varied to establish the scope and limitations of the method developed. By applying these conditions, a variety of new heterocyclic compounds bearing two tertiary phosphine oxides were successfully synthesized in moderate to excellent yields. After adjustments to the reaction conditions [Pd(OAc)2/dippf/t-BuOK], cross-coupling of secondary phosphine oxides with bulky (secondary or tertiary alkyl) substituents on the phosphorus atom was achieved. Extension of the methodology to monohalohetarenes and monohaloarenes was successfully carried out; once again, the steric and electronic properties of the halides were varied widely. The desired reaction occurred in all cases studied, giving high to excellent yields of product regardless of the nature and positions of substituents.

Consecutive Palladium Catalyzed Reactions in One-Pot Reactions

2020 ◽  
Vol 17 (5) ◽  
pp. 559-569
Author(s):  
Ingrid Caroline Vaaland ◽  
Magne Olav Sydnes
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Homogeneous Reaction ◽  
Reaction Conditions ◽  
One Pot ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed ◽  
Catalyzed Reactions

Combining palladium catalyzed reactions in one-pot reactions represents an efficient and economical use of catalyst. The Suzuki-Miyaura cross-coupling has been proven to be a reaction which can be combined with other palladium catalyzed reactions in the same pot. This mini-review will highlight some of the latest examples where Suzuki-Miyaura cross-coupling reactions have been combined with other palladium catalyzed reactions in one-pot reaction. Predominantly, examples with homogeneous reaction conditions will be discussed in addition to a few examples from the authors where Pd/C have been used as a catalyst.

scholarly journals Understanding Site Selectivity in the Palladium-Catalyzed Cross-Coupling of Allenylsilanolates

Synlett ◽  
2017 ◽  
Vol 28 (18) ◽  
pp. 2415-2420
Author(s):  
Scott Denmark ◽  
Andrea Ambrosi
Keyword(s):  
Cross Coupling ◽  
The Other ◽  
Fine Tuning ◽  
Reaction Conditions ◽  
Site Selectivity ◽  
Palladium Catalyzed ◽  
Selective Formation ◽  
Useful Yield

Allenylsilanolates can undergo cross-coupling at the α- or γ-terminus, and site selectivity appears to be determined by the intrinsic transmetalation mechanism. Fine-tuning of concentration, nucleophilicity, and steric bulk of the silanolate moiety allows for the selective formation of one isomer over the other. Whereas the α-isomer can be obtained in synthetically useful yield, the γ-isomer is favored only when employing reaction conditions that are inevitably associated with diminished reactivity.

Palladium-catalyzed cross-coupling of enamides with sterically hindered α-bromocarbonyls

2016 ◽  
Vol 52 (32) ◽  
pp. 5617-5620 ◽  
Author(s):  
Ran Ding ◽  
Zhi-Dao Huang ◽  
Zheng-Li Liu ◽  
Tian-Xiang Wang ◽  
Yun-He Xu ◽  
...  
Keyword(s):  
Amino Acid ◽  
Amino Alcohol ◽  
Cross Coupling ◽  
Reaction Conditions ◽  
Palladium Catalyzed ◽  
Sterically Hindered

Palladium-catalyzed intermolecular alkylation of enamides with α-bromo carbonyls was developed. Under mild reaction conditions, various cyclic and acyclic enamides reacted well with α-bromo carbonyls to afford the corresponding multi-substituted alkene products in good yields. The coupling products could be converted into very useful γ-amino acid, δ-amino alcohol, 1,4-dicarbonyl and γ-lactam derivatives.

scholarly journals The Quest for the Ideal Base: Rational Design of a Nickel Precatalyst Enables Mild, Homogeneous C–N Cross-Coupling

2020 ◽  
Author(s):  
Richard Liu ◽  
Joseph Dennis ◽  
Stephen L. Buchwald
Keyword(s):  
Density Functional ◽  
Rational Design ◽  
Heterogeneous Reaction ◽  
Cross Coupling ◽  
Ni Catalyst ◽  
Palladium Catalyzed ◽  
Aryl Amines ◽  
Bidentate Phosphine ◽  
Bidentate Phosphine Ligand ◽  
The Many

Palladium-catalyzed amination reactions using soluble organic bases have provided a solution to the many issues associated with heterogeneous reaction conditions. Still, homogeneous C–N cross-coupling approaches cannot yet employ bases as weak and economical as trialkylamines. Furthermore, organic base-mediated methods have not been developed for Ni(0/II) catalysis, despite some advantages of such systems over analogous Pd-based catalysts. We designed a new air-stable and easily prepared Ni(II) precatalyst bearing an electron-deficient bidentate phosphine ligand that enables the cross-coupling of aryl triflates with aryl amines using triethylamine (TEA) as base. The method is tolerant of sterically-congested coupling partners, as well as those bearing base- and nucleophile-sensitive functional groups. With the aid of density functional theory (DFT) calculations, we determined that the electron-deficient auxiliary ligands decrease both the pKa of the Ni-bound amine and the barrier to reductive elimination from the resultant Ni(II)–amido complex. Moreover, we determined that precluding Lewis acid-base complexation between the Ni catalyst and the base, due to steric factors, is important for avoiding catalyst inhibition.

Palladium-Catalyzed Cross-Coupling Reactions of 4-Tosyl­oxyquinazolines with Indoles: An Efficient Approach to 4-(1H-Indol-1-yl)quinazolines

Synthesis ◽  
2020 ◽  
Vol 53 (02) ◽  
pp. 383-390 ◽  
Author(s):  
Yiyuan Peng ◽  
Xinglin Ye ◽  
Jian Huang ◽  
Zhihong Deng ◽  
Jianjun Yuan
Keyword(s):  
Late Stage ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Indole Derivatives ◽  
Reaction Conditions ◽  
Efficient Approach ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed

In this paper, exploration of our continuous interests on late-stage derivation of quinozaline core is described. A wide array of 4-(1H-indol-1-yl)quinazolines were obtained in good to excellent yields through palladium-catalyzed cross-coupling of 4-tosyloxyquinazolines with indole derivatives under mild reaction conditions.

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

scholarly journals Microwave-Assisted Palladium-Catalyzed Cross-Coupling Reactions: Generation of Carbon–Carbon Bond

Catalysts ◽  
2019 ◽  
Vol 10 (1) ◽  
pp. 4 ◽  
Author(s):  
Kifah S. M. Salih ◽  
Younis Baqi
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Microwave Technology ◽  
Reaction Conditions ◽  
Carbon Bond ◽  
Microwave Assisted ◽  
Cross Coupling Reactions ◽  
Carbon Carbon Bond ◽  
Challenging Tasks ◽  
Palladium Catalyzed

Cross-coupling reactions furnishing carbon–carbon (C–C) bond is one of the most challenging tasks in organic syntheses. The early developed reaction protocols by Negishi, Heck, Kumada, Sonogashira, Stille, Suzuki, and Hiyama, utilizing palladium or its salts as catalysis have, for decades, attracted and inspired researchers affiliated with academia and industry. Tremendous efforts have been paid to develop and achieve more sustainable reaction conditions, such as the reduction in energy consumption by applying the microwave irradiation technique. Chemical reactions under controlled microwave conditions dramatically reduce the reaction time and therefore resulting in increase in the yield of the desired product by minimizing the formation of side products. In this review, we mainly focus on the recent advances and applications of palladium catalyzed cross-coupling carbon–carbon bond formation under microwave technology.

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