Redoxaktive NOx‐Liganden in palladiumvermittelten Prozessen

Fairlamb, Ian J. S.

doi:10.1002/ange.201411487

Cited by 21 publications

(9 citation statements)

References 71 publications

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“…In Pd-catalyzed coupling reactions of heterocycles, hydrodehalogenation is often a consequence of an inefficacious trans-metalation step. 65 Although faster oxidative addition would be expected to occur in route A (compared to route B), the subsequent concerted metalation-deprotonation of 2-hexylthiophene may not be as efficient as it would be for route B with pentafluorobenzene. Gorelsky noted that fluorine substituents, especially at the ortho position, improve the efficiency of the concerted metalation-deprotonation step.…”

Section: Articlementioning

confidence: 99%

Influence of functionality on direct arylation of model systems as a route toward fluorinated copolymers via direct arylation polymerization (DArP)

Livi¹,

Gobalasingham²,

Bundgaard

et al. 2015

J. Polym. Sci., Part A: Polym. Chem.

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A screening of direct arylation conditions on a model small molecule system is carried out to develop suitable conditions for the direct arylation polymerization (DArP) of fluorinated copolymers, which are incompatible with conditions previously utilized successfully for nonfluorinated systems. The model system features a coupling between a 2‐substituted thiophene and a pentafluorobenzene, where one of the partners was brominated. A substantial difference in reactivity is observed, demonstrating that the optimal functionalization for direct arylation between a thiophene‐based donor and a highly fluorinated acceptor is a halogenated thiophene and an unfunctionalized fluorinated unit, which is opposite of typical cross coupling reactions, where the acceptor is typically halogenated. The best conditions are applied to the copolymerization of 1,2,4,5‐tetrafluorobenzene and 2,2'‐(2,5‐bis((2‐hexyldecyl)oxy)−1,4‐phenylene)dithiophene. Polymers are free of β‐defects and significant homocoupling. This work further underscores the attractive simplicity, relevance, and ease of DArP while reconfirming its broad compatibility with increasingly popular fluorinated copolymers. © 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2015, 53, 2598–2605

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Section: Articlementioning

confidence: 99%

Influence of functionality on direct arylation of model systems as a route toward fluorinated copolymers via direct arylation polymerization (DArP)

Livi¹,

Gobalasingham²,

Bundgaard

et al. 2015

J. Polym. Sci., Part A: Polym. Chem.

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“…To our delight, the ortho ‐fluorinated product 2 a (see Table ) was obtained in 82 % yield in EtOAc. As anticipated, nitrate additives were indispensable in this transformation, and only 44 % yield of 2 a was detected in the absence of AgNO 3 (see the Supporting Information for details) …”

Section: Methodsmentioning

confidence: 99%

Selective C(sp³)−H and C(sp²)−H Fluorination of Alcohols Using Practical Auxiliaries

et al. 2018

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Selective introduction of fluorine into molecules by the cleavage of inert C-H bonds is of central academic and synthetic interest, yet remains challenging. Given the central role of alcohols in organic chemistry as the most ubiquitous building blocks, a versatile and selective C(sp )-H and C(sp )-H fluorination of simple alcohols, enabled by novel designed exo-directing groups, is described. C(sp )-H bond fluorination was achieved by using a simple acetone oxime as auxiliary, whereas a new, modular and easily accessible bidentate auxiliary was developed for the efficient and site-selective fluorination of various primary methyl, methylene, and benzylic C(sp )-H bonds. Fluorinated alcohols can readily be accessed by the removal of auxiliaries, and significantly expands the synthetic prospect of the present procedure.

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“…Polymeric 3 was completely unreactive for the formation of the precursor dimer complex ( 21 ). Both of these studies clearly highlight the benefits of using high purity palladium acetate in precatalyst formation, however more studies may be needed to establish generality …”

Section: Structure–activity Studies Of Palladium Acetatementioning

confidence: 97%

“…A recent minireview article by Fairlamb et al. provides additional discussion of the possible roles of NO x ligands in Pd catalysis …”

Section: Structure–activity Studies Of Palladium Acetatementioning

confidence: 99%

See 1 more Smart Citation

Understanding Palladium Acetate from a User Perspective

Carole

Colacot

2016

Chemistry A European J

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The behavior of palladium acetate is reviewed with respect to its synthesis, characterization, structure (in both solution and solid state), and activation pathways. In addition, comparisons of catalytic activities between pure palladium acetate and two common byproducts, Pd3 (OAc)5 (NO2 ) and polymeric [Pd(OAc)2 ]n , typically present in commercially available material are reviewed. Hence, this minireview serves as a concise guide for the users of palladium acetate from both academia and industry.

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Redoxaktive NO_x‐Liganden in palladiumvermittelten Prozessen

Cited by 21 publications

References 71 publications

Influence of functionality on direct arylation of model systems as a route toward fluorinated copolymers via direct arylation polymerization (DArP)

Influence of functionality on direct arylation of model systems as a route toward fluorinated copolymers via direct arylation polymerization (DArP)

Selective C(sp³)−H and C(sp²)−H Fluorination of Alcohols Using Practical Auxiliaries

Understanding Palladium Acetate from a User Perspective

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Redoxaktive NOx‐Liganden in palladiumvermittelten Prozessen

Cited by 21 publications

References 71 publications

Influence of functionality on direct arylation of model systems as a route toward fluorinated copolymers via direct arylation polymerization (DArP)

Influence of functionality on direct arylation of model systems as a route toward fluorinated copolymers via direct arylation polymerization (DArP)

Selective C(sp3)−H and C(sp2)−H Fluorination of Alcohols Using Practical Auxiliaries

Understanding Palladium Acetate from a User Perspective

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Product

Resources

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Redoxaktive NO_x‐Liganden in palladiumvermittelten Prozessen

Selective C(sp³)−H and C(sp²)−H Fluorination of Alcohols Using Practical Auxiliaries