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.

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.

A Palladium-Catalyzed Ullmann-Ziegler Cross-Coupling for Sterically Hindered Biaryls

Synthesis ◽  
2011 ◽  
Vol 2011 (08) ◽  
pp. 1249-1254 ◽  
Author(s):  
Richard Göttlich ◽  
Max Nüllen
Keyword(s):  
Cross Coupling ◽  
Palladium Catalyzed ◽  
Sterically Hindered

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 Palladium-catalyzed C–N and C–O bond formation of N-substituted 4-bromo-7-azaindoles with amides, amines, amino acid esters and phenols

2012 ◽  
Vol 8 ◽  
pp. 2004-2018 ◽  
Author(s):  
Rajendra Surasani ◽  
Dipak Kalita ◽  
A V Dhanunjaya Rao ◽  
K B Chandrasekhar
Keyword(s):  
Amino Acid ◽  
Bond Formation ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Amino Acid Esters ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
Acid Esters

Simple and efficient procedures for palladium-catalyzed cross-coupling reactions of N-substituted 4-bromo-7-azaindole (1H-pyrrole[2,3-b]pyridine), with amides, amines, amino acid esters and phenols through C–N and C–O bond formation have been developed. The C–N cross-coupling reaction of amides, amines and amino acid esters takes place rapidly by using the combination of Xantphos, Cs2CO3, dioxane and palladium catalyst precursors Pd(OAc)2/Pd2(dba)3. The combination of Pd(OAc)2, Xantphos, K2CO3 and dioxane was found to be crucial for the C–O cross-coupling reaction. This is the first report on coupling of amides, amino acid esters and phenols with N-protected 4-bromo-7-azaindole derivatives.

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.

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