Anion−π Interactions with Fluoroarenes

Giese, Michael; Albrecht, Markus; Rissanen, Kari

doi:10.1021/acs.chemrev.5b00156

Cited by 258 publications

(192 citation statements)

References 168 publications

(461 reference statements)

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“…The nature of the chemical reactions can be controlled by the influence of weak interactions or soft force . Therefore, many reactions are designed by exploring cooperative multiple non‐covalent interactions like hydrogen bonding, halogen bonding, hydrophobic effect, cation‐π, anion‐π, etc . Our research goal is encircled in understanding the reactivity of non‐prefunctionalized substrates by weak or noncovalent interactions .…”

Section: Resultsmentioning

confidence: 99%

Steric and Electronic Effect on C₂‐H Arylation of Sulfonamides

2019

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The ambident nature of the electrophile generated in a reaction system controls the outcome of a reaction. Electrophilic nitrenium ion which is convertible to carbenium ion via resonance was in situ generated by the reactions of iodine(III)‐reagent PhI(OAc)2 and arylsulfonamides. The nucleophile added in the reaction controls the reaction for the regiospecific ortho C−H arylation or C2‐H arylation. The electron rich arenes react with carbenium ion (electrophiles) to undergo C−H arylation. Electron donating effect (+I or +R effect) of the substituents on sulfonamide stabilizes the carbenium ion to favor oxidative coupling reaction with nucleophiles. Overall, the feasibility of C2‐H arylation of the sulfonamides has been demonstrated by steric and electronic factor that facilitates C−H arylation of sulfonamides.

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Section: Resultsmentioning

confidence: 99%

Steric and Electronic Effect on C₂‐H Arylation of Sulfonamides

2019

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“…[11] However, among metal free methods, [12] most of the coupling reactions are reported via prefunctionalization of the substrates. Selective examples of the weak interactions like anionp, [16] cation-p, [17] charge-transfer, [18] halogen bonding, [19] hydrophobic effect, [20] etc. In addition, majority of the known literatures are based on via radical pathway, using strong oxidants, with electron rich systems, etc.…”

Section: Introductionmentioning

confidence: 99%

Iodine(III) Enabled Dehydrogenative Aryl C−S Coupling by in situ Generated Sulfenium Ion

2019

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Due to the normal polarity preferences, arenes form stable complexes with thiols through SÀH···p interaction and direct dehydrogenative aryl CÀS coupling is usually restricted. We report here an umpolung based one pot and direct CÀS coupling approach under metal free and mild condition. Electrophile sulfenium ions were generated in situ from thiols using iodine(III) reagent PhI(OAc) 2 (PIDA) and subsequently used for aromatic electrophilic substitution (EArS) to synthesize diaryl sulfides. Also by using of appropriate amount of PIDA, cascaded synthesis of CÀS and S=O bonds led to aryl sulfinyl arenes in one pot. Covalent self-sorting or competitive experiments further confirmed the involvement of sulfenium ion in the EArS.

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“…The most significant of these interactions are as follows: comparatively strong hydrogen bonding, halogen bonding, π-π stacking interactions, CH···π interactions, anion/cation···π interactions and van der Waals interactions. [11][12][13][14] Supple isonicotinic hydrazide Schiff base ligands (hydrazones, R-CO-NH-N = CH-R´) and their derivatives with multifarious coordination modes are good candidates for creating supramolecular compounds [15,16] because they often acting as chelating/bridging ligands through their N and O atoms. [17][18][19] In addition, the aromatic portion of aroyl hydrazones is good candidates for spacer part of organic-inorganic materials, because not only they can act as hydrogen bond acceptors or donors, but can also provide identification sites for π-π stacking interactions as appealing supramolecular structure when coordinating to the metal ions.…”

Section: Introductionmentioning

confidence: 99%

A new supramolecular zinc(II) complex containing 4‐biphenylcarbaldehyde isonicotinoylhydrazone ligand: Nanostructure synthesis, catalytic activities and Hirshfeld surface analysis

Tyula

Zabardasti

Goudarziafshar³

et al. 2017

Applied Organom Chemis

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A new potentially tridentate hydrazone ligand, 4‐biphenylcarbaldehyde isonicotinoylhydrazone (4‐bpinh), was prepared by the condensation of biphenyl‐4‐carboxaldehyde with isonicotinic acid hydrazide. Then, its nano‐sized and single crystal of zinc complex were synthesized using sonochemical and heat gradient methods, respectively. The structure of complex, [Zn(4‐bpinh)2 Br2] (1), was determined by single‐crystal X‐ray diffraction, FT‐IR, and elemental analysis, and the nano‐structure of complex was characterized by FT‐IR, XRD, and SEM. The single crystal X‐ray structure of complex showed that the metal center has a distorted tetrahedral geometry and the hydrazone ligand acts as monodentate trough the pyridyl N atom. Moreover, the analysis of crystal structures indicates the existence of intermolecular interactions such as N/C–H⋯Br/O, N/C–H⋯π, and π⋯π stacking in the stabilization of complex structure which finally led to the formation of the three‐dimensional supramolecular structure. Also, the impact of this interactions was more studied using Hirshfeld surface analysis and corresponding 2D fingerprint plots. Furthermore, the catalytic activity of 1 was studied in the selective oxidation of various sulfides to corresponding sulfoxides using hydrogen peroxide as the oxidative agent.

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Anion−π Interactions with Fluoroarenes

Cited by 258 publications

References 168 publications

Steric and Electronic Effect on C₂‐H Arylation of Sulfonamides

Steric and Electronic Effect on C₂‐H Arylation of Sulfonamides

Iodine(III) Enabled Dehydrogenative Aryl C−S Coupling by in situ Generated Sulfenium Ion

A new supramolecular zinc(II) complex containing 4‐biphenylcarbaldehyde isonicotinoylhydrazone ligand: Nanostructure synthesis, catalytic activities and Hirshfeld surface analysis

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Anion−π Interactions with Fluoroarenes

Cited by 258 publications

References 168 publications

Steric and Electronic Effect on C2‐H Arylation of Sulfonamides

Steric and Electronic Effect on C2‐H Arylation of Sulfonamides

Iodine(III) Enabled Dehydrogenative Aryl C−S Coupling by in situ Generated Sulfenium Ion

A new supramolecular zinc(II) complex containing 4‐biphenylcarbaldehyde isonicotinoylhydrazone ligand: Nanostructure synthesis, catalytic activities and Hirshfeld surface analysis

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Product

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Steric and Electronic Effect on C₂‐H Arylation of Sulfonamides

Steric and Electronic Effect on C₂‐H Arylation of Sulfonamides