An improved procedure for the synthesis of arylboronates by palladium‐catalyzed coupling reaction of aryl halides and <i>bis</i>(pinacolato)diboron in polyethylene glycol

Lü, Jie; Guan, Zhong‐Zhi; Gao, Jian‐Wu; Zhang, Zhan‐Hui

doi:10.1002/aoc.1799

Cited by 35 publications

(18 citation statements)

References 43 publications

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“…14,41–45 In general, yields are slightly lower with the bromides as compared to the corresponding chlorides, and reaction times are slightly longer. It is believed that this increase in reaction time leads to more of the observed palladium-catalyzed hydride reduction side products in susceptible substrates.…”

Section: Resultsmentioning

confidence: 96%

Scope of the Palladium-Catalyzed Aryl Borylation Utilizing Bis-Boronic Acid

et al. 2012

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The Suzuki-Miyaura reaction has become one of the more useful tools for synthetic organic chemists. Until recently, there did not exist a direct way to make the most important component in the coupling reaction, namely the boronic acid. Current methods to make boronic acids often employ harsh or wasteful reagents to prepare boronic acid derivatives and require additional steps to afford the desired boronic acid. The scope of the previously reported palladium-catalyzed, direct boronic acid synthesis is unveiled, which includes a wide array of synthetically useful aryl electrophiles. It makes use of the newly available second generation Buchwald XPhos preformed palladium catalyst and bis-boronic acid (BBA). For ease of isolation and to preserve the often sensitive C-B bond, all boronic acids were readily converted to their more stable trifluoroborate counterparts.

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Section: Resultsmentioning

confidence: 96%

Scope of the Palladium-Catalyzed Aryl Borylation Utilizing Bis-Boronic Acid

et al. 2012

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“…Ionic liquids and polyethylene glycol have been used as alternative solvent systems for the borylation reaction. Palladium-catalyzed borylation of a wide range of aryl bromides could be done in water at room temperature using a surfactant to protect the catalyst. , A biphasic system was employed successfully for the borylation and subsequent Suzuki–Miyaura coupling, showing enhanced reactivity for substrates containing electron-withdrawing groups, heterocycles, or bulky substituents .…”

Section: Boryl Substitutionsmentioning

confidence: 99%

Diboron(4) Compounds: From Structural Curiosity to Synthetic Workhorse

et al. 2016

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“…The results from our in loco optimization demonstrate that Cu-mediated oxidative 18 F-fluorination tolerates a range of reaction conditions wider than generally described (temperature and catalyst-to-precursor ratio) [26,27,28]. This has the potential to open future perspectives, turning it into a suitable method for a larger range of molecular backbones which may not handle harsh reaction conditions.…”

Section: Resultsmentioning

confidence: 78%

“…The latent automation potential which is based on the usage of the same broadly established aqueous [ 18 F]F − pretreatment and [ 18 F]KF postprocessing mechanisms similarly to conventional radiochemistry modules, allows for the successful translation to a range of [ 18 F]fluoroarenes, including biologically relevant radiotracers [22,23,24,25]. Additionally, the relatively simple synthesis of arylboronates by palladium catalyzed coupling reactions allows the development of arylBPin building blocks that can be further used in MCR [26].…”

Section: Introductionmentioning

confidence: 99%

MCR Scaffolds Get Hotter with 18F-Labeling

et al. 2019

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Imaging techniques, such as positron emission tomography (PET), represent great progress in the clinical development of drugs and diagnostics. However, the efficient and timely synthesis of appropriately labeled compounds is a largely unsolved problem. Numerous small drug-like molecules with high structural diversity can be synthesized via convergent multicomponent reactions (MCRs). The combination of PET labeling with MCR synthesis of biologically active compounds can greatly simplify radioanalytical and imaging-based analysis. In a proof-of-concept study, we optimized robust on-site radiolabeling conditions that were subsequently applied to several structurally different drug-like MCR scaffolds (e.g., arenes, β-lactam, tetrazole, and oxazole). These labeled scaffolds were synthesized via pinacol-derived aryl boronic esters (arylBPin) by copper-mediated oxidative 18F-fluorination with radiochemical conversions (RCCs) from 15% to 76%.

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An improved procedure for the synthesis of arylboronates by palladium‐catalyzed coupling reaction of aryl halides and bis(pinacolato)diboron in polyethylene glycol

Cited by 35 publications

References 43 publications

Scope of the Palladium-Catalyzed Aryl Borylation Utilizing Bis-Boronic Acid

Scope of the Palladium-Catalyzed Aryl Borylation Utilizing Bis-Boronic Acid

Diboron(4) Compounds: From Structural Curiosity to Synthetic Workhorse

MCR Scaffolds Get Hotter with 18F-Labeling

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