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Arylboronic acid or boronate synthesis - Organic chemistry

Direct synthesis of the arylboronic acid analogues of phenylglycine via microwave-assisted four-component Ugi reaction

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α-Amino Acid synthesis by C-C coupling - Organic …

A practical, palladium-catalyzed synthesis of aryl fluorides from arylboronic acid derivatives is presented. The reaction is operationally simple and amenable to multi-gram-scale synthesis. Evaluation of the reaction mechanism suggests a single-electron-transfer pathway, involving a Pd(III) intermediate that has been isolated and characterized.

Organoboron compounds | The chemical database

In the same year, Hu et al. [] designed and synthesised monophosphine-containing polymer 117 (Figure [] ) which was then used for the room-temperature palladium-catalysed reaction between aryl chlorides and arylboronic acids.

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Stereoselective Synthesis of -Allenols by Rhodium-Catalyzed Reaction of Alkynyl Oxiranes with Arylboronic Acids. код для вставки

The catalyst system consisting of ligand 35 and Pd(OAc)2 in a 2.5:1 molar ratio was also found to be remarkably active for the cross-coupling of unactivated aryl bromides with 2-methyl- and 2-phenylphenylboronic acid. [] Moreover, compound 35 was used as a supporting ligand for the palladium-catalysed synthesis of hindered biaryls, in high-yielding palladium-catalysed couplings of arylboronic acids with a variety of heteroaryl chlorides, in Suzuki couplings at room temperature involving aryl chlorides, and in Suzuki reactions between alkylboron derivatives and aryl halides. []

Buchwald et al. [] also reported that a variety of tetra-ortho-substituted biaryls can be synthesised in 55-98% yield by Suzuki palladium-catalyzed cross-coupling reactions in which doubly ortho-substitued phosphine 32a was used as a supporting ligand. Recently, Nguyen, Huang and Buchwald [] found that a mixture of 2 mol% Pd(OAc)2 and 5 mol% ligand 33 (XPhos) represents a general precatalyst for the reaction of unactivated aryl tosylates with arylboronic acids.

All borates can be considered derivatives of boric acid, B(OH) 3

FULL TEXT Abstract: A practical, palladium-catalyzed synthesis of aryl fluorides from arylboronic acid derivatives is presented

Previously, it had been reported that, in the absence of both base and phosphine ligand, Pd(OAc)2 is able to promote the efficient synthesis of unsymmetrical biaryls by reaction of arenediazonium tetrafluoroborates with arylboronic acids. [] []

N-(4-Diphenylphoshino)phenylmethyl gluconamide (71) is another water-soluble phosphine ligand which was synthesised to perform efficient palladium-catalysed reactions of aryl halides with arylboronic acids in water. [] Interestingly, the catalyst precursor prepared from 71 and PdCl2(1,5-cyclooctadiene) in acetonitrile revealed higher activity than that synthesised from the water-soluble ligands 67 or 68. []

facile synthesis of isoflavones by the cross-coupling reaction of 3-iodochromone with arylboronic acids
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bond cross-coupling with arylboronic acid: Lam ..

AB - A four-component Ugi reaction (Ugi-4CR) utilizing formylphenyl boronic acids under mild condition was developed for the synthesis of arylboronic acid analogs. The reactions were performed in methanol and accelerated by microwave irradiation, which makes this strategy suitable for constructing boronic-containing chemical libraries. Two of the synthesized analogs were found to have cytotoxic activity against HepG2, MDA-MB231, and A549 cancer cell lines, demonstrating the potential application of this approach in developing novel boron-containing pharmaceuticals.

Arylation of Phenols with Arylboronic Acids

and and and and and (2015) Synthesis of Diverse β-Quaternary Ketones via Palladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to Cyclic Enones. Tetrahedron, 71 (35). pp. 5781-5792. ISSN 0040-4020. PMCID PMC4598955.

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Therefore, since the [18F]fluorination of arylboronic acid pinacol ester derivatives tolerates electron-poor and electro-rich arenes and various functional groups,(2) the main goal of this research work was to achieve the 18F-radiolabeling of several different molecules synthesized through MCR.

FACILE SYNTHESIS OF ISOFLAVONES BY THE CROSS …

N2 - A four-component Ugi reaction (Ugi-4CR) utilizing formylphenyl boronic acids under mild condition was developed for the synthesis of arylboronic acid analogs. The reactions were performed in methanol and accelerated by microwave irradiation, which makes this strategy suitable for constructing boronic-containing chemical libraries. Two of the synthesized analogs were found to have cytotoxic activity against HepG2, MDA-MB231, and A549 cancer cell lines, demonstrating the potential application of this approach in developing novel boron-containing pharmaceuticals.

Publications - The Suginome Research Group - 京都大学

Early in the investigation, we selected arylboronic acids as coupling partners due to their compatibility with other functional groups, ready availability, and ease of handling. Upon examining the reaction sequence from a retrosynthetic perspective, we envisioned exploiting arylsulfonate esters (3, ) as the immediate precursors to sulfonamides, and thus potential targets for Suzuki-Miyaura cross-coupling. In turn, we proposed that sulfonate esters (3) could be prepared from an aryl chlorosulfate derivative (2) via Pd-catalysis. However, contrary to our expectations, we discovered serendipitously that this coupling process generates arylsulfonyl chlorides (4) in preference to 3, and we describe herein the development and scope of a Pd-catalyzed chlorosulfonylation reaction.

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