Palladium catalyzed C(sp2)–C(sp2) bond formation. A highly regio- and chemoselective oxidative Heck C-3 alkenylation of pyrones and pyridones

RSC Advances ◽  
2015 ◽  
Vol 5 (96) ◽  
pp. 78958-78961 ◽  
Author(s):  
Hafiz Ul Lah ◽  
Faheem Rasool ◽  
Syed Khalid Yousuf
Keyword(s):  
Bond Formation ◽  
Reaction Conditions ◽  
Simple Reaction ◽  
Ligand Free ◽  
Palladium Catalyzed

Palladium catalysed ligand free highly regio- and chemoselective dehydrogenative C-3 alkenylation of pyrones and unprotected pyridones from unactivated alkenes is reported. Simple reaction conditions and broad substrate scope make the process useful.

One pot oxidative N–S bond formation to access 2-sulfenylimine chromenes

2016 ◽  
Vol 14 (2) ◽  
pp. 582-589 ◽  
Author(s):  
Ashok Kale ◽  
Madhu Chennapuram ◽  
Chiranjeevi Bingi ◽  
Jagadeesh Babu Nanubolu ◽  
Krishnaiah Atmakur
Keyword(s):  
Bond Formation ◽  
Reaction Conditions ◽  
One Pot ◽  
Simple Reaction ◽  
Catalyst Free

Synthesis of 2-sulfenylimine chromene compounds is accomplished in a one-pot, catalyst-free, five-component reaction in toluene. When aniline was employed as nucleophile formation of hexahydrobenzofuran-2-N-phenyl carboxamide was observed. Excellent yields, simple reaction conditions high compatibility are the advantages of this protocol.

First reusable ligand-free palladium catalyzed C–P bond formation of aryl halides with trialkylphosphites in neat water

RSC Advances ◽  
2014 ◽  
Vol 4 (99) ◽  
pp. 55732-55737 ◽  
Author(s):  
Nasser Iranpoor ◽  
Habib Firouzabadi ◽  
Khashayar Rajabi Moghadam ◽  
Somayeh Motavalli
Keyword(s):  
Bond Formation ◽  
Aryl Halides ◽  
Neat Water ◽  
Ligand Free ◽  
Palladium Catalyzed

Ligand-free palladium catalyzed Ullmann biaryl synthesis: ‘household’ reagents and mild reaction conditions

2019 ◽  
Vol 21 (5) ◽  
pp. 995-999 ◽  
Author(s):  
Xinchi Gong ◽  
Jie Wu ◽  
Yunge Meng ◽  
Yulan Zhang ◽  
Long-Wu Ye ◽  
...  
Keyword(s):  
Hydrazine Hydrate ◽  
Room Temperature ◽  
Reaction Conditions ◽  
Ligand Free ◽  
Palladium Catalyzed ◽  
Biaryl Synthesis

A palladium catalysed Ullmann biaryl synthesis has been developed using hydrazine hydrate as the reducing reagent at room temperature.

ChemInform Abstract: First Reusable Ligand-Free Palladium Catalyzed C-P Bond Formation of Aryl Halides with Trialkylphosphites in Neat Water.

ChemInform ◽  
2015 ◽  
Vol 46 (17) ◽  
pp. no-no
Author(s):  
Nasser Iranpoor ◽  
Habib Firouzabadi ◽  
Khashayar Rajabi Moghadam ◽  
Somayeh Motavalli
Keyword(s):  
Bond Formation ◽  
Aryl Halides ◽  
Neat Water ◽  
Ligand Free ◽  
Palladium Catalyzed

scholarly journals Palladium-Catalyzed Approach to Allenic Aromatic Ethers and First Total Syntheses of Terricollene A

2021 ◽  
Author(s):  
Chaofan Huang ◽  
Fuchun Shi ◽  
Yifan Cui ◽  
Can Li ◽  
Jie Lin ◽  
...  
Keyword(s):  
Bond Formation ◽  
Reaction Conditions ◽  
Formation Reaction ◽  
Total Syntheses ◽  
Palladium Catalyzed

A palladium-catalyzed C-O bond formation reaction between phenols and allenylic carbonates to give 2,3-allenic aromatic ethers with decent to excellent yields under mild reaction conditions has been described. A variety...

scholarly journals Palladium-Catalyzed Oxidative Allylic Alkylation of N-Hydroxy­imides

Synlett ◽  
2019 ◽  
Vol 31 (01) ◽  
pp. 87-91
Author(s):  
Narasimham Ayyagari ◽  
Sunil Kumar Sunnam ◽  
Milind M. Ahire ◽  
Minxi Yang ◽  
Kevin Ngo ◽  
...  
Keyword(s):  
Allylic Alkylation ◽  
Reaction Conditions ◽  
Ligand Free ◽  
Palladium Catalyzed

A palladium-catalyzed oxidative C–H allylic alkylation of N-hydroxyimides has been developed. This transformation provided valuable N-allyloxypyrrolidinediones in moderate to excellent yields using operationally simple, ligand free, and mild reaction conditions. The reaction tolerated broad and variable substituents on allylarenes and N-hydroxyimides.

Environment Friendly and Recyclable CuCl2-mediated C-S Bond Coupling Strategy Using DMEDA as Ligand, Base and Solvent

Synthesis ◽  
2021 ◽  
Author(s):  
Guodong Shen ◽  
Qichao Lu ◽  
Zeyou Wang ◽  
Weiwei Sun ◽  
Yalin Zhang ◽  
...  
Keyword(s):  
Catalytic System ◽  
Bond Formation ◽  
Environmentally Friendly ◽  
Industrial Applications ◽  
Reaction Conditions ◽  
Environment Friendly ◽  
Economic Strategy ◽  
Formation Reaction ◽  
Simple Reaction ◽  
Coupling Strategy

Simple reaction conditions and recyclable reagents are an irreplaceable advantage for environmentally friendly industrial applications. An environment friendly, recyclable and economic strategy was developed to synthesize diaryl chalcogenides by the CuCl2 catalyzed C-S bond formation reaction via iodobenzenes and benzenethiols/1,2-diphenyldisulfanes using N,N’-dimethylethane-1,2-diamine (DMEDA) as ligand, base and solvent. For these reactions, especially the reactions of diiodobenzenes and aminobenzenethiols/disulfanediyldianilines, a range of substrates is compatible to give the corresponding products in good to excellent yields. Both the reaction reagents of the catalytic system (CuCl2/DMEDA) are inexpensive, conveniently separable and recyclable for more than 5 cycles.

Aminocarbonylation of N-Containing Heterocycles with Aromatic Amines Using Mo(CO)6

Synthesis ◽  
2018 ◽  
Vol 50 (07) ◽  
pp. 1521-1526 ◽  
Author(s):  
Sandrine Piguel ◽  
Marius Mamone ◽  
Jessy Aziz ◽  
Julie Le Bescont
Keyword(s):  
Aromatic Amines ◽  
Molybdenum Hexacarbonyl ◽  
Reaction Conditions ◽  
Simple Reaction ◽  
Aniline Derivatives ◽  
Palladium Catalyzed

We describe herein the palladium-catalyzed aminocarbonylation of nitrogen-containing heterocycles with aniline derivatives using molybdenum hexacarbonyl as a CO solid source, expanding the scope of the limited examples. This method is compatible with a variety of substitutions on the aniline moiety. The simple reaction conditions include easily available Pd(dppf)Cl2 catalyst, DBU as base in DMF at 120 °C for 3 hours in sealed tube thereby leading to the isolation of 21 compounds with yields ranging from 18 to 82%. We also show that double aminocarbonylation reactions are possible in satisfactory yields regarding both coupling partners.

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.

Pd Catalyzed N1/N4 Arylation of Piperazine for Synthesis of Drugs, Biological and Pharmaceutical Targets: An Overview of Buchwald Hartwig Amination Reaction of Piperazine in Drug Synthesis

2018 ◽  
Vol 15 (2) ◽  
pp. 208-220 ◽  
Author(s):  
Vaibhav Mishra ◽  
Tejpal Singh Chundawat
Keyword(s):  
Bond Formation ◽  
Catalyst Design ◽  
Biologically Active ◽  
Reaction Conditions ◽  
Biological Targets ◽  
Amination Reaction ◽  
Drug Synthesis ◽  
Substituted Piperazine ◽  
Approved Drugs ◽  
Fda Approved Drugs

Background: Substituted piperazine heterocycles are among the most significant structural components of pharmaceuticals. N1/N4 substituted piperazine containing drugs and biological targets are ranked 3rd in the top most frequent nitrogen heterocycles in U.S. FDA approved drugs. The high demand of N1/N4 substituted piperazine containing biologically active compounds and U.S. FDA approved drugs, has prompted the development of Pd catalyzed C-N bond formation reactions for their synthesis. Buchwald-Hartwig reaction is the key tool for the synthesis of these compounds. Objective: This review provides strategies for Pd catalyzed C-N bond formation at N1/N4 of piperazine in the synthesis of drugs and biological targets with diverse use of catalyst-ligand system and reaction parameters. Conclusion: It is clear from the review that a vast amount of work has been done in the synthesis of N1/N4 substituted piperazine containing targets under the Pd catalyzed Buchwald-Hartwig amination of aryl halides by using different catalyst-ligand systems. These methods have become increasingly versatile as a result of innovation in catalyst design and improvements in reaction conditions. This review gives an overview of recent utilization of Buchwald-Hartwig amination reaction in drug/target synthesis.

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