Regioselective palladium-catalysed cross-coupling reactions: a powerful synthetic tool

Kapdi, Anant R.; Prajapati, Dipak

doi:10.1039/c4ra07895k

Cited by 38 publications

(15 citation statements)

References 160 publications

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“…Halogenated compounds 12 and 13 were borylated in 65, 82, 84 and 93% yield. In contrast to earlier reports and controls without catalyst, cross-coupling was not detected, highlighting the chemoselectivity of the method ( Kapdi and Prajapati, 2014 ). In the case of anilines with electron donating groups, yields were initially lower than 50%, surely owed to the stability of the corresponding diazonium compounds which simply did not react fast enough.…”

Section: Resultscontrasting

confidence: 98%

Mild, Organo-Catalysed Borono-Deamination as a Key to Late-Stage Pharmaceutical Precursors and 18F-Labelled Radiotracers

Pérez-García

Riss

2022

Front. Chem.

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A tris(pentafluorophenyl)borane catalysed method for the synthesis of boronic acid esters from aromatic amines in yields of up to 93% was devised. Mild conditions, benign reagents, short reaction times, low temperatures and a wide substrate scope characterize the method. The reaction was found applicable to the synthesis of boronic acid ester derivatives of complex drug molecules in up to 86% isolated yield and high purity suitable for labelling. These boronates were subsequently labelled with [18F]fluoride ion in radiochemical yields of up to 55% with and even without isolation of the boronate-intermediate.

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Section: Resultscontrasting

confidence: 98%

Mild, Organo-Catalysed Borono-Deamination as a Key to Late-Stage Pharmaceutical Precursors and 18F-Labelled Radiotracers

Pérez-García

Riss

2022

Front. Chem.

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“…Continuing on the success obtained with the new N‐heterocyclic carbene ligands that were recently introduced by our research group for the selective arylation of 2,6‐dibromopyridine structural motif yielding biologically active Combretastatin analogues, we envisaged the possible complexation of some of the ligands reported therein along with a few new ones. Herein, we have synthesised the water‐soluble sulfonate NHC ligands (7 a‐c) by using the known procedure .…”

Section: Resultsmentioning

confidence: 99%

New Water‐Soluble N‐Heterocyclic Carbene‐Palladium Complexes as Promising Anti‐Tumor Agents: Investigating DNA and Protein Interactions

et al. 2018

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This investigation focuses on the synthesis and characterization of three new, water-soluble palladium complexes, with potential to overcome the drawbacks of platinum-based anti-cancer drugs. The complexes contain small N-heterocyclic carbene (NHC) ligands, having groups that impart water solubility. The anti-cancer effects of these complexes were evaluated in two different cancer cell lines, namely,HeLa, a cervical cancer cell line and A549,adenocarcinoma human alveolar basal epithelial cell line. Cytotoxicity of the complexes was compared with cisplatin, an established platinum-based anti-cancer moiety, using the MTT assay (MTT is 3-(4,5-dimethylthiazol-2-yl)-2,5diphenyltetrazolium bromide). Aqueous solutions of the synthesized complexes demonstrated significant cytotoxicity in both the cell lines. The synthesized metal complexes resulted in a stronger, cytotoxic effect in A549 cells (lung cancer cells), as compared to cisplatin. Furthermore, interaction of these palladium compounds with DNA was studied using gel electrophoresis and spectrometry methods. The result suggested that the complexes interacted with DNA via intercalation. Interaction with BSA (Bovine Serum Albumin) was investigated using UV-Vis spectroscopy suggesting positive interaction of palladium complex with BSA proteins. Furthermore, fluorescence studies revealed quenching of protein fluorescence thus, indicating dynamic quenching mechanism with the number of association sites being calculated as~1.

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“…The structure of 2,3-diiodinated diarylacetylene compounds are further conrmed by X-ray diffraction methods for three coupling products, 1,2-diiodo-3-((4-(triuoromethyl)phenyl) Although various approaches for regioselective Sonogashira cross-coupling have been previously reported, [34][35][36][37][38][39][40][41][42][43][44][45][46] a plausible catalytic cycle for regioselective Sonogashira cross-coupling of 5-substituted-1,2,3-triiodobenzene is proposed in Scheme 3. Oxidative addition by Pd 0 at the terminal C-I position, the less sterically hindered and more accessible position forming Pd II intermediate A.…”

Section: Entrymentioning

confidence: 99%

Palladium-catalyzed highly regioselective mono and double Sonogashira cross-coupling reactions of 5-substituted-1,2,3-triiodobenzene under ambient conditions

et al. 2020

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Regioselective palladium-catalysed cross-coupling reactions: a powerful synthetic tool

Cited by 38 publications

References 160 publications

Mild, Organo-Catalysed Borono-Deamination as a Key to Late-Stage Pharmaceutical Precursors and 18F-Labelled Radiotracers

Mild, Organo-Catalysed Borono-Deamination as a Key to Late-Stage Pharmaceutical Precursors and 18F-Labelled Radiotracers

New Water‐Soluble N‐Heterocyclic Carbene‐Palladium Complexes as Promising Anti‐Tumor Agents: Investigating DNA and Protein Interactions

Palladium-catalyzed highly regioselective mono and double Sonogashira cross-coupling reactions of 5-substituted-1,2,3-triiodobenzene under ambient conditions

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