Photochemical Activation of a Hydroxyquinone-Derived Phenyliodonium Ylide by Visible Light: Synthetic and Mechanistic Investigations

Jalali, Mona; Ho, Curtis C.; Fuller, Rebecca O.; Lucas, Nigel T.; Ariafard, Alireza; Bissember, Alex C.

doi:10.1021/acs.joc.0c02592

Cited by 8 publications

(1 citation statement)

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“…Illustration of the occurrence of halogen bonding between building blocks in some crystalline materials. (a) Tris(1,10-phenanthroline)-iron bis(tribromide) hemikis(dibromine) [C 36 H 24 Fe N 6 2+ ,2(Br 3 – ),0.5(Br 2 )], (b) bis(2,2′:6′,2″-terpyridine)-cobalt bis(iodide) tetrakis(1,3,5-trifluoro-2,4,6-tris(iodo)benzene) methanol solvate [C 30 H 22 CoN 6 2+ ,4(C 6 F 3 I 3 ),CH 4 O,2(I – )], (c) di(isoquinolin-2-yl)iodanium tris(iodine) triiodide [C 18 H 14 IN 2 + ,I 3 – ,3(I 2 )], (d) diphenyliodonium chloride [C 12 H 10 I + ,Cl – ], (e) bis(2-fluorophenyl)iodonium chloride [C 12 H 8 F 2 I + ,Cl – ], (f) bis(diphenyliodonium) tetrachloro-platinum [2(C 12 H 10 I + ),Cl 4 Pt 2– ], (g) bis(acetonitrile) bromine [2(C 2 H 3 N),Br 2 ]; (h) C 70 fullerene di-iodine [I 2 ,C 70 ], (i) 3,6-dioxo-2-(phenyliodaniumyl)cyclohexa-1,4-dien-1-olate [C 12 H 7 IO 3 ], (j) 3,4,5-tribromo-2,6-dimethylpyridine [C 7 H 6 Br 3 N], (k) 1-(1-diazo-2,2,2-trifluoroethyl)-1,2-benziodoxol-3(1H)-one [C 9 H 4 F 3 IN 2 O 2 ], and (l) 2,3,5,6-tetrafluoro-4-iodopyridine toluene solvate [C 7 H 8 ,C 5 F 4 IN] . For clarity, some molecules in (a–d), (f) and (g) are omitted.…”

Section: Illustrative Crystal Systems Featuring Halogen Bondingmentioning

confidence: 99%

Definition of the Halogen Bond (IUPAC Recommendations 2013): A Revisit

Varadwaj,

Marques

et al. 2024

Crystal Growth & Design

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that fail to include the fundamental, underlying concept of (electrophilic) σand p-/π-hole theory and orbital-based charge transfer interactions that accompany halogen bond formation. An electrophilic σ-hole, or p-/π-hole, is an electron-density-deficient region of positive polarity (and positive potential) on the electrostatic surface on the side of halogen along, or orthogonal to, a covalently bonded halogen in a molecular entity that leads to the development of a noncovalent interaction�a halogen bond� when in close proximity to an electron-density-rich nucleophilic region on the same or another identical or different molecular entity, with which it interacts. This Article re-examines the characteristic features of the halogen bond and lists a wide variety of donors and acceptors that participate in halogen bonding. We add caveats that are essential for identifying halogen bonding in chemical systems, necessary for the appropriate use of the terminologies involved. Illustrative examples of chemical systems that feature inter-and intramolecular halogen bonds and other noncovalent interactions in the crystalline phase are given, together with a case study of some dimer systems using first-principles calculations. We also point out that the π-hole/belt (or p-hole/belt) that may develop on the surface of a halogen derivative in halogenated molecules may be prone to forming a π-hole/belt (or p-hole/belt) halogen bond when in close proximity to nucleophiles on another similar or different molecular entity.

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Section: Illustrative Crystal Systems Featuring Halogen Bondingmentioning

confidence: 99%

Definition of the Halogen Bond (IUPAC Recommendations 2013): A Revisit

Varadwaj,

Marques

et al. 2024

Crystal Growth & Design

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Hypervalent Iodine (III)‐Based Complexation for Chiroptical Supramolecular Glass, Deep Eutectic Solvent and Luminescent Switch

An,

Hao,

Xing

2024

Advanced Materials

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Hypervalent iodine(III) have widely been utilized for organic synthetic reagents. They are also recognized as positive charge‐assisted, exceptionally robust biaxial halogen bond donors, while their potential in supramolecular materials is barely explored. This work reports a cyclic diaryliodonium ion as biaxial halogen bonding donor that displays remarkable binding affinity toward phenanthroline or acridine acceptors with chiral pendants. Biaxial halogen bonding enables chiroptical evolution in solution, allowing for rational control over supramolecular chirality. Leveraging their strong binding affinity, the halogen bonding complexes manifested amorphous properties and deep eutectic behavior in the solid state. Capitalizing on these attributes, this work achieves the successful preparation of supramolecular glasses and deep eutectic solvents. Additionally, halogen bonding appended light irradiation‐triggered luminescence through a hydrogen atom transfer process, showing applications in anti‐counterfeit and display.

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Recent Advances in Radical Reactions of Azo Compounds

2023

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Azo compounds have attracted much attention in the past decades, due to their unique properties. Recently, the free radical strategy has been widely applied to the chemical transformations of azobenzenes, dialkyl azodicarboxylates, mainly including hydrogenation and functionalization of N=N double bond, and N-functionalization reactions via the cleavage of the N=N double bonds. In this review, we systematically summarized these reactions as well as their mechanisms are discussed.

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Photochemical Activation of a Hydroxyquinone-Derived Phenyliodonium Ylide by Visible Light: Synthetic and Mechanistic Investigations

Cited by 8 publications

References 50 publications

Definition of the Halogen Bond (IUPAC Recommendations 2013): A Revisit

Definition of the Halogen Bond (IUPAC Recommendations 2013): A Revisit

Hypervalent Iodine (III)‐Based Complexation for Chiroptical Supramolecular Glass, Deep Eutectic Solvent and Luminescent Switch

Recent Advances in Radical Reactions of Azo Compounds

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