ChemInform Abstract: Chelation-Assisted Cross-Coupling of Anilines Through in situ Activation as Diazonium Salts with Boronic Acids under Ligand-, Base-, and Salt-Free Conditions.

ChemInform ◽  
2013 ◽  
Vol 44 (48) ◽  
pp. no-no
Author(s):  
Roxan Joncour ◽  
Nicolas Susperregui ◽  
Noel Pinaud ◽  
Karinne Miqueu ◽  
Eric Fouquet ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Boronic Acids ◽  
Diazonium Salts ◽  
In Situ Activation

Chelation-Assisted Cross-Coupling of Anilines through In Situ Activation as Diazonium Salts with Boronic Acids under Ligand-, Base-, and Salt-Free Conditions

2013 ◽  
Vol 19 (28) ◽  
pp. 9291-9296 ◽  
Author(s):  
Roxan Joncour ◽  
Nicolas Susperregui ◽  
Noël Pinaud ◽  
Karinne Miqueu ◽  
Eric Fouquet ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Boronic Acids ◽  
Diazonium Salts ◽  
In Situ Activation

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.

Gold-catalysed cross-coupling between aryldiazonium salts and arylboronic acids: probing the usefulness of photoredox conditions

2016 ◽  
Vol 52 (65) ◽  
pp. 10040-10043 ◽  
Author(s):  
Thomas Cornilleau ◽  
Philippe Hermange ◽  
Eric Fouquet
Keyword(s):  
Cross Coupling ◽  
Gold Catalysis ◽  
Boronic Acids ◽  
Diazonium Salts ◽  
Arylboronic Acids ◽  
Mild Conditions ◽  
Biaryl Compounds

Combining gold catalysis and photoredox processes allowed the synthesis of biaryl compounds from diazonium salts and boronic acids under mild conditions.

Photosensitizer-Free, Gold-Catalyzed C-C Cross-Coupling of Boronic Acids and Diazonium Salts Enabled by Visible Light

2017 ◽  
Vol 359 (9) ◽  
pp. 1522-1528 ◽  
Author(s):  
Sina Witzel ◽  
Jin Xie ◽  
Matthias Rudolph ◽  
A. Stephen K. Hashmi
Keyword(s):  
Visible Light ◽  
Cross Coupling ◽  
Boronic Acids ◽  
Diazonium Salts ◽  
Free Gold

Recent Advances in Metal-Catalyzed, Electrochemical Coupling Reactions of sp2 Halides/Boronic Acids and sp3 Centers

Synthesis ◽  
2020 ◽  
Author(s):  
Zachary J. Gale-Day
Keyword(s):  
Cross Coupling ◽  
Short Review ◽  
Boronic Acids ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Organic Electrochemistry ◽  
Recent Advances ◽  
Electrochemical Coupling ◽  
Metal Catalyzed

AbstractTraditionally, metal-catalyzed cross-coupling reactions rely on stable but expensive metals, such as palladium. However, the recent development of synthetic organic electrochemistry allows for in situ redox manipulations, expanding the use of cheaper, abundant and sustainable metals, such as nickel and copper as efficient cross-coupling catalysts. This short review covers the recent advances in metal-catalyzed electrochemical coupling reactions, with a focus on reactions of sp2 electrophiles and nucleophiles with sp3 coupling partners to form both C–C and C–heteroatom bonds.1 Introduction2 Nickel-Catalyzed C–C sp2–sp3 Coupling Reactions3 Coupling of Aryl Groups with Heteroatomic Nuclei4 Conclusion

A Mild and Simple Method for Making MIDA Boronates

2020 ◽  
Author(s):  
Aidan Kelly ◽  
Peng-Jui (Ruby) Chen ◽  
Jenna Klubnick ◽  
Daniel J. Blair ◽  
Martin D. Burke
Keyword(s):  
Organic Synthesis ◽  
Boronic Acids ◽  
Simple Method ◽  
Direct Preparation ◽  
Synthesis Procedure ◽  
Harsh Conditions

<div> <div> <div> <p>Existing methods for making MIDA boronates require harsh conditions and complex procedures to achieve dehydration. Here we disclose that a pre-dried form of MIDA, MIDA anhydride, acts as both a source of the MIDA ligand and an in situ desiccant to enable a mild and simple MIDA boronate synthesis procedure. This method expands the range of sensitive boronic acids that can be converted into their MIDA boronate counterparts. Further utilizing unique properties of MIDA boronates, we have developed a MIDA Boronate Maker Kit which enables the direct preparation and purification of MIDA boronates from boronic acids using only heating and centrifuge equipment that is widely available in labs that do not specialize in organic synthesis. </p> </div> </div> </div>

A Photoactivatable α5β1-Specific Integrin Ligand

2018 ◽  
Author(s):  
Roshna Vakkeel ◽  
Aleeza Farrukh ◽  
Aranzazu del Campo
Keyword(s):  
Cellular Response ◽  
Light Exposure ◽  
Matrix Composition ◽  
Cellular Behavior ◽  
Dynamic Variations ◽  
In Situ Activation ◽  
Controlled Exposure ◽  
Cellular Behaviour ◽  
Integrin Ligand

In order to study how dynamic changes of α5β1 integrin engagement affect cellular behaviour, photoactivatable derivatives of α5β1 specific ligands are presented in this article. The presence of the photoremovable protecting group (PRPG) introduced at a relevant position for integrin recognition, temporally inhibits ligand bioactivity. Light exposure at cell-compatible dose efficiently cleaves the PRPG and restores functionality. Selective cell response (attachment, spreading, migration) to the activated ligand on the surface is achieved upon controlled exposure. Spatial and temporal control of the cellular response is demonstrated, including the possibility to in situ activation. Photoactivatable integrin-selective ligands in model microenvironments will allow the study of cellular behavior in response to changes in the activation of individual integrins as consequence of dynamic variations of matrix composition.

The Total Synthesis of Rhabdastrellic Acid A

2018 ◽  
Author(s):  
Yaroslav Boyko ◽  
Christopher Huck ◽  
David Sarlah
Keyword(s):  
Total Synthesis ◽  
Late Stage ◽  
Cross Coupling ◽  
Side Chains ◽  
General Strategy ◽  
Modular Approach ◽  
Linear Sequence ◽  
Generating Sequence ◽  
First Time

<div>The first total synthesis of rhabdastrellic acid A, a highly cytotoxic isomalabaricane triterpenoid, has been accomplished in a linear sequence of 14 steps from commercial geranylacetone. The prominently strained <i>trans-syn-trans</i>-perhydrobenz[<i>e</i>]indene core characteristic of the isomalabaricanes is efficiently accessed in a selective manner for the first time through a rapid, complexity-generating sequence incorporating a reductive radical polyene cyclization, an unprecedented oxidative Rautenstrauch cycloisomerization, and umpolung 𝛼-substitution of a <i>p</i>-toluenesulfonylhydrazone with in situ reductive transposition. A late-stage cross-coupling in concert with a modular approach to polyunsaturated side chains renders this a general strategy for the synthesis of numerous family members of these synthetically challenging and hitherto inaccessible marine triterpenoids.</div>

The Merger of CF3SO2Na and Palladium Catalysis to Enable Decarboxylative Cross-Coupling for the Synthesis of Aromatic Ketones under Room Temperature

2021 ◽  
Author(s):  
Pan Xie ◽  
Cheng Xue ◽  
Cancan Wang ◽  
Dongdong Du ◽  
Sanshan Shi
Keyword(s):  
Visible Light ◽  
Room Temperature ◽  
Palladium Catalysis ◽  
Cross Coupling ◽  
Boronic Acids ◽  
Aromatic Ketones ◽  
Aryl Ketones ◽  
Oxocarboxylic Acids

A CF3SO2Na/Pd(OAc)2 co-catalyzed strategy is developed to produce aryl ketones via visible-light-induced decarboxylative cross-coupling of α-oxocarboxylic acids and aryl boronic acids. This process was perfomed under air at room temperature,...

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