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.

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.

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.

Room temperature nickel-catalyzed cross-coupling of aryl-boronic acids with thiophenols: synthesis of diarylsulfides

2020 ◽  
Vol 18 (13) ◽  
pp. 2447-2458 ◽  
Author(s):  
Amit Bhowmik ◽  
Mahesh Yadav ◽  
Rodney A. Fernandes
Keyword(s):  
Room Temperature ◽  
Cross Coupling ◽  
Boronic Acids ◽  
Arylboronic Acids

A mild and easy to operate NiCl2/2,2′-bipyridine-catalyzed cross-coupling of thiophenols with arylboronic acids has been developed for the synthesis of symmetric and unsymmetric diarylsulfides at room temperature and in air.

scholarly journals Cross coupling of benzylammonium salts with boronic acids using a well-defined N-heterocyclic carbene–palladium(ii) precatalyst

RSC Advances ◽  
2019 ◽  
Vol 9 (10) ◽  
pp. 5738-5741 ◽  
Author(s):  
Tao Wang ◽  
Jiarui Guo ◽  
Xiaojuan Wang ◽  
Han Guo ◽  
Dingli Jia ◽  
...  
Keyword(s):  
Bond Activation ◽  
Cross Coupling ◽  
Boronic Acids ◽  
Arylboronic Acids

N-heterocyclic carbene–palladium(ii)-catalyzed cross-coupling of benzylammonium salts with arylboronic acids for the synthesis of diarylmethane derivatives via C–N bond activation has been developed.

Rhodium-Catalyzed Asymmetric Addition of Arylboronic Acids to Glyoxylates: Access to Optically Active Substituted Mandelic Acid Esters

Synlett ◽  
2019 ◽  
Vol 30 (14) ◽  
pp. 1693-1697
Author(s):  
Diao Chen ◽  
Jian-Guo Liu ◽  
Xu Zhang ◽  
Ming-Hua Xu
Keyword(s):  
Catalytic System ◽  
Mandelic Acid ◽  
Optically Active ◽  
Antiplatelet Drug ◽  
Reaction Conditions ◽  
Formal Synthesis ◽  
Arylboronic Acids ◽  
Synthetic Utility ◽  
Enantioselective Addition ◽  
Acid Esters

A rhodium-catalyzed enantioselective addition of glyoxylates to arylboronic acids promoted by a simple chiral sulfinamide-based olefin ligand under mild reaction conditions is described. The reaction provides access to a variety of optically active substituted mandelic acid esters in good yields with up to 83% ee. The catalytic system is also applicable to pyruvate addition. The synthetic utility of this method is highlighted by a formal synthesis of the antiplatelet drug clopidogrel.

ChemInform Abstract: Oxidative Biaryl Coupling of Thiophenes and Thiazoles with Arylboronic Acids Through Palladium Catalysis: Otherwise Difficult C4-Selective C-H Arylation Enabled by Boronic Acids.

ChemInform ◽  
2011 ◽  
Vol 42 (24) ◽  
pp. no-no
Author(s):  
Sylvia Kirchberg ◽  
Satoshi Tani ◽  
Kirika Ueda ◽  
Junichiro Yamaguchi ◽  
Armido Studer ◽  
...  
Keyword(s):  
Palladium Catalysis ◽  
Boronic Acids ◽  
Arylboronic Acids ◽  
Biaryl Coupling

scholarly journals Unusual (Z)-selective palladium(ii)-catalysed addition of aryl boronic acids to vinylaziridines

2014 ◽  
Vol 12 (45) ◽  
pp. 9113-9115 ◽  
Author(s):  
JieXiang Yin ◽  
Theresa Mekelburg ◽  
Christopher Hyland
Keyword(s):  
Ring Opening ◽  
Boronic Acids ◽  
Arylboronic Acids ◽  
Reaction Proceeds ◽  
Opening Process

The palladium(ii)-catalysed addition of arylboronic acids to vinylaziridines has been developed. This reaction proceeds via an insertion/ring-opening process to provide (E)-allylsulfonamides. This stereoselectivity is complimentary to existing methods that typically proceed via an SN2′ mechanism to yield (Z)-allylic systems.

Influence of fluorine substituents on the properties of phenylboronic compounds

2018 ◽  
Vol 90 (4) ◽  
pp. 677-702 ◽  
Author(s):  
Jan T. Gozdalik ◽  
Agnieszka Adamczyk-Woźniak ◽  
Andrzej Sporzyński
Keyword(s):  
Analytical Chemistry ◽  
Organic Synthesis ◽  
Rapid Development ◽  
Hydrolytic Stability ◽  
Spectroscopic Properties ◽  
Boronic Acids ◽  
Lewis Acidity ◽  
Materials Chemistry ◽  
Special Group ◽  
Arylboronic Acids

AbstractRapid development of research on the chemistry of boronic acids is connected with their applications in organic synthesis, analytical chemistry, materials’ chemistry, biology and medicine. In many applications Lewis acidity of boron atoms plays an important role. Special group of arylboronic acids are fluoro-substituted compounds, in which the electron withdrawing character of fluorine atoms influences their properties. The present paper deals with fluoro-substituted boronic acids and their derivatives: esters, benzoxaboroles and boroxines. Properties of these compounds, i.e. acidity, hydrolytic stability, structures in crystals and in solution as well as spectroscopic properties are discussed. In the next part examples of important applications are given.

scholarly journals A convenient route to symmetrically and unsymmetrically substituted 3,5-diaryl-2,4,6-trimethylpyridines via Suzuki–Miyaura cross-coupling reaction

2016 ◽  
Vol 12 ◽  
pp. 835-845 ◽  
Author(s):  
Dariusz Błachut ◽  
Joanna Szawkało ◽  
Zbigniew Czarnocki
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
High Yield ◽  
Reaction Conditions ◽  
Arylboronic Acids ◽  
Cross Coupling Reaction ◽  
Convenient Route

A series of differently substituted 3,5-diaryl-2,4,6-trimethylpyridines were prepared and characterized using the Suzuki–Miyaura coupling reaction with accordingly selected bromo-derivatives and arylboronic acids. The reaction conditions were carefully optimized allowing high yield of isolated products and also the construction of unsymmetrically substituted diarylpyridines, difficult to access by other methods.

Photoinduced hydroxylation of arylboronic acids with molecular oxygen under photocatalyst-free conditions

2019 ◽  
Vol 21 (18) ◽  
pp. 4971-4975 ◽  
Author(s):  
Yu-Ting Xu ◽  
Chen-Yuan Li ◽  
Xiao-Bo Huang ◽  
Wen-Xia Gao ◽  
Yun-Bing Zhou ◽  
...  
Keyword(s):  
Molecular Oxygen ◽  
Boronic Acids ◽  
Arylboronic Acids

We disclose a photoinduced aerobic hydroxylation of boronic acids under photocatalyst-free conditions, providing a green entry to phenols and alcohols.

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