Synthesis of 4-sulfonatobenzylphosphines and their application in aqueous-phase palladium-catalyzed cross-coupling

Moore, Jane N.; Laskay, Nicholas M.; Duque, Kevin S.; Kelley, Steven P.; Rogers, Robin D.; Shaughnessy, Kevin H.

doi:10.1016/j.jorganchem.2014.11.011

Cited by 12 publications

(3 citation statements)

References 35 publications

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“…4-Carboxy-4′-Methoxybiphenyl (11). From 4-carboxyphenylboronic acid and 4-bromoanisole: Yield: 96 mg (90%), white solid, mp: 250−253 °C (lit.…”

Section: -Methoxybiphenyl (3)mentioning

confidence: 99%

“…mp: 250.0−251.7 °C). 56 4-Carboxy-4′-Methoxybiphenyl (11). From 4-methoxyphenylboronic acid and 4-bromobenzoic acid: Yield: 95 mg (89%), white solid, mp: 250−253 °C (lit mp: 250.0−251.7 °C).…”

Section: -Methoxybiphenyl (3)mentioning

confidence: 99%

“…Numerous efforts have been made in order to apply water as solvent in this reaction; however, in most cases, organic co-solvents had to be used. Furthermore, isolation and purification of products often required organic solvents for extraction and column chromatography. − The use of a water-soluble Pd(II)-sulfonated triphenylphosphine complex to catalyze this process in aqueous reaction medium was first studied by Casalnuovo and Calabrese in 1990 . Main efforts of later research were focused on the application of various water-soluble Pd-tertiary phosphine, − palladacycle, , and Pd-N-heterocyclic carbene , (Pd-NHC) complex catalysts in aqueous solution, often with microwave irradiation .…”

mentioning

confidence: 99%

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Organic Solvent-Free, Pd(II)-Salan Complex-Catalyzed Synthesis of Biaryls via Suzuki–Miyaura Cross-Coupling in Water and Air

et al. 2018

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With use of a Pd(II)-sulfosalan complex as a water-soluble catalyst, we have developed an efficient synthesis of biaryls via Suzuki−Miyaura cross-coupling in water under aerobic conditions. The water-insoluble target molecules were isolated by simple filtration in analytical purity after washing with 0.01 M aqueous HCl (20 examples). In most cases, palladium contamination was below 5 ppm considered acceptable for active pharmaceutical ingredients. The established method is scalable, reproducible, and provides biaryl products in isolated yields up to 91%.

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“…4-Carboxy-4′-Methoxybiphenyl (11). From 4-carboxyphenylboronic acid and 4-bromoanisole: Yield: 96 mg (90%), white solid, mp: 250−253 °C (lit.…”

Section: -Methoxybiphenyl (3)mentioning

confidence: 99%

Section: -Methoxybiphenyl (3)mentioning

confidence: 99%

mentioning

confidence: 99%

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Organic Solvent-Free, Pd(II)-Salan Complex-Catalyzed Synthesis of Biaryls via Suzuki–Miyaura Cross-Coupling in Water and Air

et al. 2018

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Synthesis of Hydrophilic Phosphorus Ligands and Their Application in Aqueous‐Phase Metal‐Catalyzed Reactions

Schlatzer

Breinbauer

2020

Adv Synth Catal

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Transition metal‐catalyzed reactions in aqueous media are experiencing a constant increase in interest. In homogenous catalysis the use of water as a solvent offers advantages in cost, safety, the possibility of two‐phase catalysis and simplified separation strategies. In the life sciences, transition metal catalysis in aqueous systems enables the ligation or modification of biopolymers in buffer systems or even in their cellular environment. In biocatalysis, aqueous systems allow the simultaneous use of enzymes and transition metal catalysts in cascade reactions. The use of water‐soluble phosphine ligands still represents the most reliable and popular strategy for transferring metal catalysts into the aqueous phase. This review summarizes the recent advancements in this field since 2009 and describes current synthetic strategies for the preparation of hydrophilic phosphines and phosphites. In addition, recent applications of transition metal catalysis in aqueous solvents using these hydrophilic ligands are presented.

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ChemInform Abstract: Synthesis of 4‐Sulfonatobenzylphosphines and Their Application in Aqueous‐Phase Palladium‐Catalyzed Cross‐Coupling.

et al. 2015

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Synthesis of 4-sulfonatobenzylphosphines and their application in aqueous-phase palladium-catalyzed cross-coupling

Cited by 12 publications

References 35 publications

Organic Solvent-Free, Pd(II)-Salan Complex-Catalyzed Synthesis of Biaryls via Suzuki–Miyaura Cross-Coupling in Water and Air

Organic Solvent-Free, Pd(II)-Salan Complex-Catalyzed Synthesis of Biaryls via Suzuki–Miyaura Cross-Coupling in Water and Air

Synthesis of Hydrophilic Phosphorus Ligands and Their Application in Aqueous‐Phase Metal‐Catalyzed Reactions

ChemInform Abstract: Synthesis of 4‐Sulfonatobenzylphosphines and Their Application in Aqueous‐Phase Palladium‐Catalyzed Cross‐Coupling.

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