A practical and general ipso iodination of arylboronic acids using N-iodomorpholinium iodide (NIMI) as a novel iodinating agent: mild and regioselective synthesis of aryliodides

RSC Advances ◽  
2015 ◽  
Vol 5 (103) ◽  
pp. 84910-84919 ◽  
Author(s):  
R. H. Tale ◽  
G. K. Toradmal ◽  
V. B. Gopula
Keyword(s):  
Molecular Iodine ◽  
Boronic Acids ◽  
Regioselective Synthesis ◽  
Arylboronic Acids

A mild and efficient protocol for the ipso-iodination of aryl boronic acids using N-iodomorpholinium iodide (NIMI) generated in situ from morpholine and molecular iodine as a novel iodinating agent has been developed.

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.

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>

scholarly journals Practical iridium-catalyzed direct α-arylation of N-heteroarenes with (hetero)arylboronic acids by H2O-mediated H2 evolution

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Liang Cao ◽  
He Zhao ◽  
Rongqing Guan ◽  
Huanfeng Jiang ◽  
Pierre. H. Dixneuf ◽  
...  
Keyword(s):  
Structural Modification ◽  
Universal Access ◽  
Boronic Acids ◽  
Direct Access ◽  
Bidentate Ligands ◽  
H2 Evolution ◽  
Arylboronic Acids ◽  
Coupling Strategy ◽  
General Method ◽  
Operational Simplicity

AbstractDespite the widespread applications of 2-(hetero)aryl N-heteroarenes in numerous fields of science and technology, universal access to such compounds is hampered due to the lack of a general method for their synthesis. Herein, by a H2O-mediated H2-evolution cross-coupling strategy, we report an iridium(III)-catalyzed facile method to direct α-arylation of N-heteroarenes with both aryl and heteroaryl boronic acids, proceeding with broad substrate scope and excellent functional compatibility, oxidant and reductant-free conditions, operational simplicity, easy scalability, and no need for prefunctionalization of N-heteroarenes. This method is applicable for structural modification of biomedical molecules, and offers a practical route for direct access to 2-(hetero)aryl N-heteroarenes, a class of potential cyclometalated C^N ligands and N^N bidentate ligands that are difficult to prepare with the existing α-C-H arylation methods, thus filling an important gap in the capabilities of synthetic organic chemistry.

DNA‐Compatible Click Reaction Employing In Situ Generated Azides from Boronic Acids

2021 ◽  
Vol 1 (5) ◽  
Author(s):  
Yulong An ◽  
Hao Yan ◽  
Zhenzhen Dong ◽  
Alexander L. Satz
Keyword(s):  
Click Reaction ◽  
Boronic Acids

Acetic acid mediated regioselective synthesis of 2,4,5-trisubstituted thiazoles by a domino multicomponent reaction

2019 ◽  
Vol 43 (22) ◽  
pp. 8644-8650 ◽  
Author(s):  
Mohit Saroha ◽  
Jitender M. Khurana
Keyword(s):  
Acetic Acid ◽  
Multicomponent Reaction ◽  
Regioselective Synthesis ◽  
Domino Reaction ◽  
Thiazole Derivatives ◽  
Active Methylene

Acetic acid mediated regioselective synthesis of novel 2,4,5-trisubstituted thiazole derivatives has been reported by a domino reaction of thiosemicarbazide and aldehydes/ketones/isatin, to generate thiosemicarbazones (in situ) followed by addition of arylglyoxal and active methylene/activated C–H acids/pyrazole/indole in ethanol at 80 °C.

Synthesis of Solution-Phase Phosphoramidite and Phosphite Ligand Libraries and Their In Situ Screening in the Rhodium-Catalyzed Asymmetric Addition of Arylboronic Acids

2007 ◽  
Vol 9 (3) ◽  
pp. 407-414 ◽  
Author(s):  
Richard B. C. Jagt ◽  
Patrick Y. Toullec ◽  
Ebe P. Schudde ◽  
Johannes G. de Vries ◽  
Ben L. Feringa ◽  
...  
Keyword(s):  
Solution Phase ◽  
Asymmetric Addition ◽  
Arylboronic Acids

Palladium-catalysed cyclisation of ynamides and propargyl tethered iodosulfonamides with boronic acids leading to benzosultams

2021 ◽  
Author(s):  
K. Sandeep ◽  
Alla Siva Reddy ◽  
K. C. Kumara Swamy
Keyword(s):  
Boronic Acids ◽  
Arylboronic Acids ◽  
Synthetic Utility ◽  
Convenient Route

A convenient route to benzo[d]isothiazole and benzo[e][1,2]thiazine scaffolds using ynamides and arylboronic acids under [Pd]-catalysis is reported; the synthetic utility has been demonstrated by a gram-scale synthesis.

Facile one-pot synthesis of 2-amino-1,3,4-oxadiazole tethered peptidomimetics by molecular-iodine-mediated cyclodeselenization

2017 ◽  
Vol 41 (19) ◽  
pp. 11225-11229 ◽  
Author(s):  
L. Santhosh ◽  
C. Srinivasulu ◽  
S. Durgamma ◽  
Girish Prabhu ◽  
Vommina V. Sureshbabu
Keyword(s):  
Molecular Iodine ◽  
One Pot ◽  
Highly Efficient ◽  
One Pot Synthesis

Mild and highly efficient I2 and Et3N aided cyclodeselenization of in situ generated selenosemicarbazide is described to obtain 2-amino-1,3,4-oxadiazole peptidomimetics.

Iodine-mediated C–N and C–S bond formation: regioselective synthesis of benzo[4,5]imidazo[2,1-b]thiazoles

2017 ◽  
Vol 41 (1) ◽  
pp. 75-80 ◽  
Author(s):  
Sethurajan Ambethkar ◽  
Muthalu Vellimalai ◽  
Vediappen Padmini ◽  
Nattamai Bhuvanesh
Keyword(s):  
Reaction Time ◽  
Intramolecular Cyclization ◽  
Simple Procedure ◽  
Bond Formation ◽  
Molecular Iodine ◽  
Regioselective Synthesis ◽  
Thiazole Derivatives ◽  
Short Reaction Time ◽  
Metal Free

The regioselective synthesis of benzo[4,5]imidazo[2,1-b]thiazole derivatives via amination (C–N) and intramolecular cyclization (C–S) reactions in the presence of molecular iodine has been reported. This method is base and metal free and features inexpensive catalysts, with a simple procedure and a short reaction time.

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