Palladium-catalyzed highly regioselective hydroaminocarbonylation of aromatic alkenes to branched amides

2017 ◽  
Vol 15 (14) ◽  
pp. 2910-2913 ◽  
Author(s):  
Jinping Zhu ◽  
Bao Gao ◽  
Hanmin Huang
Keyword(s):  
Reaction Conditions ◽  
Efficient Catalyst ◽  
Palladium Catalyzed

Pd(t-Bu3P)2 has been successfully identified as an efficient catalyst for the hydroaminocarbonylation of aromatic alkenes to branched amides under relatively mild reaction conditions.

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.

ChemInform Abstract: A General and Efficient Catalyst for Palladium-Catalyzed C-O Coupling Reactions of Aryl Halides with Primary Alcohols.

ChemInform ◽  
2010 ◽  
Vol 42 (4) ◽  
pp. no-no
Author(s):  
Saravanan Gowrisankar ◽  
Alexey G. Sergeev ◽  
Pazhamalai Anbarasan ◽  
Anke Spannenberg ◽  
Helfried Neumann ◽  
...  
Keyword(s):  
Aryl Halides ◽  
Coupling Reactions ◽  
Primary Alcohols ◽  
Efficient Catalyst ◽  
Palladium Catalyzed

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 direct ortho-ethoxycarbonylation of azobenzenes and azoxybenzenes with diethyl azodicarboxylate

2015 ◽  
Vol 13 (34) ◽  
pp. 9083-9092 ◽  
Author(s):  
Ning Xu ◽  
Dengke Li ◽  
Yicheng Zhang ◽  
Lei Wang
Keyword(s):  
Reaction Conditions ◽  
Palladium Catalyzed ◽  
Diethyl Azodicarboxylate

A palladium-catalyzed direct ortho-ethoxycarbonylation of azobenzenes and azoxybenzenes with diethyl azodicarboxylate (DEAD) was developed under mild reaction conditions.

Palladium-catalyzed one-pot cycloaddition reactions of thioureas with 3H-indol-3-ones generated in situ from 2-alkynyl arylazides: rapid and efficient access to imidazoloindolines

2020 ◽  
Vol 7 (21) ◽  
pp. 3480-3485
Author(s):  
Ping Li ◽  
Boyu Zhu ◽  
Yao Xu ◽  
Zhiqiang Zhou ◽  
Guiwen Hu ◽  
...  
Keyword(s):  
Cycloaddition Reactions ◽  
Reaction Conditions ◽  
One Pot ◽  
One Pot Synthesis ◽  
Efficient Access ◽  
Palladium Catalyzed

An efficient palladium-catalyzed one-pot synthesis of imidazoloindolines from 2-alkynyl arylazides under mild reaction conditions has been described.

Palladium-Catalyzed Anti-Markovnikov Oxidation of Aromatic and Aliphatic Alkenes to Terminal Acetals and Aldehydes

Synthesis ◽  
2020 ◽  
Author(s):  
Yasuyuki Ura
Keyword(s):  
Organic Compounds ◽  
Catalytic System ◽  
Recent Progress ◽  
Short Review ◽  
Nucleophilic Attack ◽  
Reaction Conditions ◽  
Terminal Alkenes ◽  
Palladium Catalyzed ◽  
Substrate Addition ◽  
Cyclic Alkenes

AbstractCatalytic anti-Markovnikov (AM) oxidation of terminal alkenes can provide terminally oxyfunctionalized organic compounds. This short review mainly summarizes our recent progress on the Pd-catalyzed AM oxidations of aromatic and aliphatic terminal alkenes to give terminal acetals (oxidative acetalization) and aldehydes (Wacker-type oxidation), along with related reports. These reactions demonstrate the efficacy of the PdCl2(MeCN)2/CuCl/electron-deficient cyclic alkenes/O2 catalytic system. Notably, electron-deficient cyclic alkenes such as p-benzoquinones (BQs) and maleimides are key additives that facilitate nucleophilic attack of oxygen nucleophiles on coordinated terminal alkenes and enhance the AM selectivity. BQs also function to oxidize Pd(0) depending on the reaction conditions. Several other factors that improve the AM selectivity, such as the steric demand of the nucleo­philes, slow substrate addition, and halogen-directing groups, are also discussed.1 Introduction2 Anti-Markovnikov Oxidation of Aromatic Alkenes to Terminal Acetals­3 Anti-Markovnikov Oxidation of Aromatic Alkenes to Aldehydes4 Anti-Markovnikov Oxidation of Aliphatic Alkenes to Terminal Acetals­5 Anti-Markovnikov Oxidation of Aliphatic Alkenes to Aldehydes6 Conclusion

scholarly journals Azidophosphonium salt-directed chemoselective synthesis of (E)/(Z)-cinnamyl-1H-triazoles and regiospecific access to bromomethylcoumarins from Morita–Baylis–Hillman adducts

2020 ◽  
Vol 16 ◽  
pp. 1579-1587
Author(s):  
Soundararajan Karthikeyan ◽  
Radha Krishnan Shobana ◽  
Kamarajapurathu Raju Subimol ◽  
J Helen Ratna Monica ◽  
Ayyanoth Karthik Krishna Kumar
Keyword(s):  
The Novel ◽  
Reaction Conditions ◽  
Efficient Catalyst ◽  
Direct Transformation ◽  
Chemoselective Synthesis

The direct transformation of Morita–Baylis–Hillman (MBH) adducts into molecules of interest is a crucial process wherein allylic hydroxy-protected or halogenated MBH adducts are commonly preferred. Herein, we report an azidophosphonium salt (AzPS)-catalysed straight forward protocol for synthesising structurally demanding (E)/(Z)-cinnamyl-1H-1,2,3-triazoles and halomethylcoumarins from MBH adducts. The novel methodology, efficient catalyst, and direct utilization of MBH adducts under mild reaction conditions qualify the reported procedures as powerful synthetic tools.

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