Suzuki–Miyaura reactions of 3,5-dichloro-2,4,6-trifluoropyridine

Sharif, Muhammad; Shoaib, Khurram; Ahmed, Sajjad; Iqbal, Jamshed; Abilov, Zharylkasyn A.; Spannenberg, Anke; Langer, Peter

doi:10.1016/j.tetlet.2016.05.041

Cited by 12 publications

(6 citation statements)

References 35 publications

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“…Therefore, numerous compounds have been synthesized by different research groups to obtain the most effective catalyst in the SMC reaction. [ 34,44–52 ]…”

Section: Discussionmentioning

confidence: 99%

Importance of some factors on the Suzuki‐Miyaura cross‐coupling reaction

Akkoç

2021

J Chinese Chemical Soc

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This review was designed to give an overview of the significant parameters in Suzuki‐Miyaura coupling (SMC) reactions, which are a powerful tool for the formation of the carbon–carbon (CC) bond. Since the SMC reaction depends on factors such as solvent, base, temperature, time, catalyst amount, substituent in aryl halides, and molar ratios of the substrates, all these parameters should be screened for a successful SMC reaction. After finding the optimum reaction conditions, the SMC reaction's products of boronic acid derivatives with aryl halides can be obtained in high yields.

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“…Therefore, numerous compounds have been synthesized by different research groups to obtain the most effective catalyst in the SMC reaction. [ 34,44–52 ]…”

Section: Discussionmentioning

confidence: 99%

Importance of some factors on the Suzuki‐Miyaura cross‐coupling reaction

Akkoç

2021

J Chinese Chemical Soc

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“…Different arylated 2,4,6-trifluoropyridines 86 and 88 were obtained in moderate to good yields using commercially available 3,5-dichloro-2,4,6-trifluoropyridine (Scheme 12). 103 Scheme 12 Synthesis of 3-aryl-or 3,5-diaryl-2,4,6-trifluoropyridine derivatives…”

Section: Syn Thesismentioning

confidence: 99%

Arylpyridines: A Review from Selective Synthesis to Atropisomerism

Pomarański

Czarnocki²

2018

Synthesis

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Multiply arylated heterocycles are interesting structures with highly useful functions and fascinating optoelectronic and biological properties. Pyridines are an important class of compounds, playing a role in various fields of chemistry. When the pyridine ring is connected to other aromatic systems, novel stereochemical outcomes may arise. This work summarizes different methodologies applied for the synthesis of substituted arylpyridine derivatives and summarizes stereochemical phenomena resulting from atropisomerism present in certain arylated pyridines.1 Introduction2 Arylpyridines Containing meta- and para-Substituted Phenyl Groups2.1 Arylpyridine Derivatives as Amphetamine Analogues Markers2.2 Site-Selective Synthesis of Arylpyridines3 Atropisomerism in Arylpyridines Containing ortho-Substituted Phenyl Groups3.1 Synthesis of Arylpyridines Containing ortho-Substituted Phenyl Groups3.2 Other Methods for the Preparation of Arylated Pyridines4 Fully Substituted Pyridine Derivatives4.1 Site-Selective Synthesis of Fully Arylated Pyridines4.3 Atropisomerism in Densely Substituted Arylpyridines Containing ortho-Substituted Phenyl Groups5 Enantioselective Synthesis of Arylpyridine Derivatives6 Conclusion

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“…To study the effects in more detail, convenient synthetic access to (poly)chlorinated triphenylbenzenes 5 is required. In contrast to the plethora of well‐explored Suzuki–Miyaura cross‐coupling of aryl halides with aryl boron species, the use of di‐ and poly‐chlorinated reactants has been mostly devoted to access polychlorinated biphenyl (PCB) derivatives for ecotoxicity and analytical property studies . In order to get access to triphenylbenzenes 5 we followed two synthetic strategies involving a cross‐coupling as the key step (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

Columnar Propeller‐Like 1,3,5‐Triphenylbenzenes: Probing the Effect of Chlorine on the Suzuki Cross‐Coupling and Liquid Crystalline Properties

et al. 2020

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Suzuki cross-couplings either between chlorinated N-methyliminodiacetic acid (MIDA)-protected aryl boronates and 1,3,5-tribromobenzene or between chlorinated aryl bromides and phenyltrisboronic species to star-shaped 1,3,5-triphenylbenzenes with different substitution patterns and chloro substituents at the outer phenyl rings were studied. The chlorinated precursors required for the respective reaction were synthesized and characterized. Depending on the used coupling reaction target triphenylbenzenes were isolated in yields between 42 % and 88 %. Their mesomorphic properties were in- [a] 2190 fluenced by the substitution pattern and number of peripheral chlorine atoms. Triphenylbenzene with 3,5-alkoxy substitution and H in para-position self-assembled into either columnar hexagonal (Col h ) mesophases or a soft crystal. While threefold chloro substitution in meta-position of the outer phenyl rings led to stable room temperature Col ho phases, triphenylbenzenes with threefold para-chloro or 3,5-dichloro substitution were non-mesomorphic. Based on X-ray diffraction data a helical packing model for the observed phases similar to that of related alkoxy-substituted triphenylbenzenes was proposed.properties and a decrease of phase transition temperatures were independently reported for bent-core liquid crystals by Twieg [9,10] and for ionic liquid crystals by Binnemans. [11] Scheme 1. Selected liquid crystalline pseudoazulenes (1, 2) and indene derivative 3. [7,8] Scheme 2. dated. To study the effects in more detail, convenient synthetic access to (poly)chlorinated triphenylbenzenes 5 is required. In contrast to the plethora of well-explored Suzuki-Miyaura crosscoupling of aryl halides with aryl boron species, [21][22][23][24][25] the use of di-and poly-chlorinated reactants has been mostly devoted to access polychlorinated biphenyl (PCB) derivatives for ecotoxicity and analytical property studies. [26][27][28][29][30][31][32][33] In order to get access to triphenylbenzenes 5 we followed two synthetic strategies involving a cross-coupling as the key step (Scheme 3). Compound 5 is derived either from Suzuki-Miyaura cross-coupling between aryl boronic species 6 [e.g., N-methyliminodiacetic acid (MIDA) boronates [34][35][36][37][38][39] ] and 1,3,5-tribromobenzene 7 (route A) or alternatively, by the connection of aryl bromides 8 and 1,3,5-phenyltrisboronic species 9 (e.g., pinacol boronate) (route B). The results towards the synthesis of compounds 5 and study of their mesomorphic properties are reported below. Scheme 4. Synthesis of precursors 6 and 8 (numbering for NMR assignment; for details see also the Supporting Information). 2191Scheme 3. Retrosynthetic pathways to star-shaped triphenylbenzenes 5.

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Suzuki–Miyaura reactions of 3,5-dichloro-2,4,6-trifluoropyridine

Cited by 12 publications

References 35 publications

Importance of some factors on the Suzuki‐Miyaura cross‐coupling reaction

Importance of some factors on the Suzuki‐Miyaura cross‐coupling reaction

Arylpyridines: A Review from Selective Synthesis to Atropisomerism

Columnar Propeller‐Like 1,3,5‐Triphenylbenzenes: Probing the Effect of Chlorine on the Suzuki Cross‐Coupling and Liquid Crystalline Properties

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