Reaction Of Iodide Research Articles

Palladium‐Catalyzed Domino Synthesis of Sulfone‐Containing 1,3‐Enynes from Simple Alkynes and Sulfonyl Iodides

A palladium‐catalyzed domino radical sulfonylation and alkynylation of simple alkynes has been developed for the rapid construction of privileged scaffolds containing sulfone and 1,3‐enyne motifs. The reaction of sulfonyl iodide with simple alkynes proceeded smoothly under mild conditions to afford a variety of sulfone‐containing 1,3‐enynes in good yields and with excellent selectivities.

Au(I)/Au(III)-Catalyzed Sulfonylation of Aryl Iodides for the Synthesis of Various Functionalized Aryl Sulfones.

A gold-catalyzed sulfonylation reaction of aryl iodides with different sodium sulfinates facilitated by the ligand-enabled Au(I)/Au(III) redox catalysis was developed. In the reaction of gold-catalyzed C-S coupling, a variety of functionalized sodium sulfinates, such as CF3, CHF2, CH3, and alkyl groups, can react smoothly with aryl iodides to directly construct diversely functionalized aryl sulfones. This gold-catalyzed sulfonylation offers a complementary method for synthesizing functionalized aryl sulfones with electron-donating groups.

Investigation of the reaction of hydrogen iodide with a chlorine atom in the atmosphere above the sea

By the method of resonant fluorescence (RF) of chlorine atoms and iodine atoms, the rate constant of the reaction of a chlorine atom with hydrogen iodide at a temperature of 298 K. The values of the reaction constants measured by both methods turned out to be quite close. The role of this reaction in the chemistry of the troposphere above the surface of the oceans is discussed.

Construction of Fe3O4@Dop-Triazine-CuCl2 as a novel and green nanocatalyst for C–Se coupling reaction of heterocyclic compounds

In this research, we first fabricated Fe3O4@Dop-Triazine-CuCl2 nanocatalyst by simple method, then its catalytic activity was investigated in the preparation of various derivatives of aryl-heteroaryl and di-heteroaryl selenides through C–Se coupling reactions of aryl iodides with powder selenium and various derivatives of heterocyclic compounds (with active C–H bonds). The catalyst exhibited spherical morphology with a diameter of approximately 20–30 nm and a magnetic saturation moment of 50.032 emu/g. The hydrocarbon content was measured to be around 12% by weight. In this method, a wide range of aryl-heteroaryl and di-heteroaryl selenides (36 examples) were synthesized with high yields (85–97%) using catalytic amount of the Fe3O4@Dop-Triazine-CuCl2 nanomaterial in the presence of KHCO3 in [BMIM]PF6 as solvent. This method has several remarkable features, which can be mentioned as follows: the synthesis of aryl-heteroaryl and di-heteroaryl selenide derivatives with high yields, performing the reactions in a suitable time (4 h), the applicability of this catalytic system for a wide range of substrates, the use of ionic liquid as solvent, high efficiency of Fe3O4@Dop-Triazine-CuCl2 catalyst, simple separation and high reusability of nanocatalyst.

Low‐valent Tungsten Catalyzed Carbonylative Sonogashira Coupling Reactions of Aryl Iodides with Alkynes

AbstractA low‐valent tungsten catalyzed carbonylative Sonogashira coupling reactions has been established. The present protocol utilizes inexpensive and readily available W(CO)6 as precatalyst and proceeds in the presence of atmospheric CO, providing a practical method to a series of functionalized alkynones and indoxyls compounds under mild reaction conditions. Moreover, the simple reaction system, good functional group tolerance and broad substrate scope enable the application of this transformation in the synthesis of functionalized carbonyl‐containing molecules.

Simultaneous tracking of ultrafast surface and gas-phase dynamics in solid-gas interfacial reactions.

Real-time detection of intermediate species and final products at the surface and near-surface in interfacial solid-gas reactions is critical for an accurate understanding of heterogeneous reaction mechanisms. In this article, an experimental method that can simultaneously monitor the ultrafast dynamics at the surface and above the surface in photoinduced heterogeneous reactions is presented. This method relies on a combination of mass spectrometry and femtosecond pump-probe spectroscopy. As a model system, the photoinduced reaction of methyl iodide on and above a cerium oxide surface is investigated. The species that are simultaneously detected from the surface and gas-phase present distinct features in the mass spectra, such as a sharp peak followed by an adjacent broad shoulder. The sharp peak is attributed to the species detected from the surface, while the broad shoulder is due to the detection of gas-phase species above the surface, as confirmed by multiple experiments. By monitoring the evolution of the sharp peak and broad shoulder as a function of the pump-probe time delay, transient signals are obtained that describe the ultrafast photoinduced reaction dynamics of methyl iodide on the surface and in the gas-phase. Finally, SimION simulations are performed to confirm the origin of the ions produced on the surface and in the gas-phase.

Ligand-Enabled Palladium-Catalyzed [3 + 2] Annulation of Aryl Iodides with Maleimides via C(sp3)-H Activation.

Palladium-catalyzed intermolecular [3 + 2] annulation reactions via C-H activation represent a powerful and charming tool for assembling cyclopentanes. Herein, we have developed a strategy for the palladium-catalyzed intermolecular alkene-relayed annulation reaction of aryl iodides and maleimides via C(sp3)-H activation for the construction of polycyclic structures. In contrast to directed-group-enabled intermolecular maleimide-relayed [3 + 2] annulation reactions, this protocol stands out for its utilization of aryl iodides as substrates. Notably, monoprotected amino acids played a crucial role as ligands in this reaction, which is rarely observed in C-H activation reactions initiated with organohalides.

Enhanced optoelectrical properties and stability of solvent-based perovskite solar cells using ellagic acid additives

Perovskite solar cells (PSCs) with solution-based fabrication processes deserve a simple and controllable fabrication process to produce cost-effective new-generation solar cells. Increasing optoelectrical properties of the light-harvesting perovskite layer during the fabrication process is used to enhance photovoltaic efficiency and the stability of PSCs. Here, ellagic acid was added into the lead iodide precursor to control the reaction of lead iodide with formamidinium iodide to generate a perovskite layer with enlarged grains. The obtained results showed the ellagic acid additive reduced charge recombination losses within solar cells and prompted charge transfer from perovskite to electron transporting layer and hole transporting layer, recording a champion efficiency of 22.04 % along with an open circuit voltage of 1.095 V, short-circuit current density of 24.17 mA cm−2, and fill factor of 78.94 %. In addition, the ellagic acid-based PSCs showed considerable stability improvement against the humidity and light irradiance compared to the control PSCs. It can be concluded that the ellagic acid additive may push the PSCs further to commercialization.

Photoinduced Pd-Catalyzed Intramolecular 6-endo Heck Reaction of Alkyl Halides.

A novel photocatalytic palladium-induced 6-endo-selective alkyl Heck reaction of unactivated alkyl iodides and alkyl bromides has been described. This strategy facilitates the gentle and efficient synthesis of a variety of 5-phenyl-1,2,3,6-tetrahydropyridine derivatives. It demonstrates a broad substrate tolerance and excellent 6-endo selectivity. Unlike the high-temperature requirements of traditional alkyl Heck reactions, this transformation efficiently proceeds at room temperature and shows significant promise for industrial-scale applications. Mechanistic investigations reveal that this alkyl Heck reaction proceeds via a hybrid palladium-radical process.

Water-Dispersible, Magnetically Recyclable Heterogeneous Cobalt Catalyst for C-C and C-N Cross-Coupling Reactions in Aqueous Media.

A cobalt catalyst supported on an iron oxide core, denoted as γ-Fe2O3@PEG@THMAM-Co, has been prepared and characterized by Fourier transform infrared spectroscopy, X-ray diffraction, field emission scanning electron microscopy, transmission electron microscopy, energy-dispersive X-ray mapping, thermogravimetry differential thermogravimetry, vibrating sample magnetometry, and inductively coupled plasma. Polyhydroxy end groups in the shell make the catalyst particles dispersible in water, allowing Hiyama, Suzuki, and C-N cross-coupling reactions of aryl iodides and bromides. The catalyst could be recovered by magnetic decantation and reused for at least five successive runs with a negligent decrease in its activity or changes in its morphology. Water as a solvent without requiring additives, surfactants, or organic co-solvents, as well as an abundant and low-cost cobalt catalyst combined with facile recovery, low leaching, and scalability, provides an environmentally and economically attractive alternative to established palladium-catalyzed C-C and C-N coupling reactions.

Crystal structure of polymeric bis-(3-amino-1H-pyrazole)-cadmium diiodide.

The reaction of cadmium iodide with 3-amino-pyrazole (3-apz) in ethano-lic solution leads to tautomerization of the ligand and the formation of crystals of the title compound, catena-poly[[di-iodido-cadmium(II)]-bis-(μ-3-amino-1H-pyrazole)-κ2 N 2:N 3;κ2 N 3:N 2], [CdI2(C3H5N3)2] n or [CdI2(3-apz)2] n . Its asymmetric unit consists of a half of a Cd2+ cation, an iodide anion and a 3-apz mol-ecule. The Cd2+ cations are coordinated by two iodide anions and two 3-apz ligands, generating trans-CdN4I2 octa-hedra, which are linked into chains by pairs of the bridging ligands. In the crystal, the ligand mol-ecules and iodide anions of neighboring chains are linked through inter-chain hydrogen bonds into a di-periodic network. The inter-molecular contacts were qu-anti-fied using Hirshfeld surface analysis and two-dimensional fingerprint plots, revealing the relative qu-anti-tative contributions of the weak inter-molecular contacts.

Gold-Catalyzed C-N Cross-Coupling Reactions of Aryl Iodides with Alkyl Nitriles or Silver Cyanate.

We have gold-catalyzed C-N cross-couplings of aryl iodides with aliphatic nitriles. Although nitriles are usually challenging nitrogen cross-coupling partners, they could be activated by base-mediated deprotonation and isomerization. The method utilizes widely available substrates in moderate to good yields to provide various N-aryl compounds. In addition, a similar strategy could be extended to the cross-couplings of aryl iodides with silver cyanate. The protocol features high humidity/air tolerance and works inter- and intramolecularly.

Ratiometric fluorescence and colorimetric strategies for assessing activity of butyrylcholinesterase in human serum using g-C3N4 nanosheets, silver ion and o-phenylenediamine.

Ratiometric fluorescence and colorimetric strategies for detecting activity of butyrylcholinesterase (BChE) in human serum were developed by using g-C3N4 nanosheets, silver ion (Ag+) and o-phenylenediamine (OPD) as chromogenic agents. The oxidation-reduction reaction of OPD and Ag+ generates 2,3-diaminophenazine (oxOPD). Under exciation at 370nm, g-C3N4 nanosheets and oxOPD emit fluorescence at 440nm (F440) and 560nm (F560), respectively. Additionally, oxOPD exhibits quenching ability towards g-C3N4 nanosheets via photoinduced electron transfer (PET) process. Thiocholine (TCh), as a product of BChE-catalyzed hydrolysis reaction of butylthiocholine iodide (BTCh), can coordinate with Ag+ intensively, and consequently diminish the amount of free Ag+ in the testing system. Less amount of free Ag+ leads to less production of oxOPD, resulting in less fluorescence quenching towards g-C3N4 nanosheets as well as less fluorescence emission of oxOPD. Therefore, by using g-C3N4 nanosheets and oxOPD as fluorescence indicators, the intensity ratio of their fluorescence (F440/F560) was calculated and employed to evaluate the activity of BChE. Similarly, the color variation of oxOPD indicated by the absorbance at 420nm (ΔA420) was monitored for the same purpose. These strategies were validated to be sensitive and selective for detecting BChE activity in human serum, with limits of detection (LODs) of 0.1 U L-1 for ratiometric fluorescence mode and 0.7 U L-1 for colorimetric mode.

Copper-Catalyzed Three-Component Synthesis of β-Hydroxysulfides from Styrene Oxide, Aryl Iodide, and Carbon Disulfide.

A copper-catalyzed three-component coupling reaction of styrene oxide, aryl iodide, and carbon disulfide for the construction of β-hydroxysulfides has been developed. In this process, readily available CS2 was used as the sulfur source to construct C-S bonds for the synthesis of phenyl-β-hydroxysulfides and (benzo[d]thiazol)-β-hydroxysulfides. This process features mild reaction conditions, simple operation, and wide substrate scope (>50 examples).

Palladium-Catalyzed Decarboxylative Annulation Reaction of Aryl Iodides and Methyl 2-Haloarenecarboxylates.

A ligand-free palladium-catalyzed and norbornadiene-mediated annulation reaction of iodoarenes with methyl 2-haloarenecarboxylates is reported. The sequentially accomplished reaction comprises intermolecular C-H arylation, followed by intramolecular decarboxylative annulation, affording various valuable phenanthrenes. This reaction protocol could be expanded to triphenylene syntheses whereby norbornene was the cocatalyst. Interestingly, the decarboxylation of methyl esters was accomplished via solvent-mediated CMe-O bond cleavages.

Water-Promoted Mild and General Michaelis-Arbuzov Reaction of Triaryl Phosphites and Aryl Iodides by Palladium Catalysis.

A Pd-catalyzed relatively general Michaelis-Arbuzov reaction of triaryl phosphites and aryl iodides for preparing useful aryl phosphonates was developed. Interestingly, water can greatly facilitate the reaction through a water-participating phosphonium intermediate rearrangement process, which also makes the reaction conditions rather mild. In comparison with the known methods, this reaction is milder and more general, as it exhibits excellent functional group tolerance, can be applied to various triaryl phosphites and aryl iodides, and can be extended to aryl phosphonites and phosphinites. A gram-scale reaction with a low catalyst loading also revealed its practicality and potential in large-scale preparation.

Investigation into the Reaction of Hydrogen Iodide with a Chlorine Atom in the Atmosphere above the Sea

Investigation into the Reaction of Hydrogen Iodide with a Chlorine Atom in the Atmosphere above the Sea

Regioselective Arylation of Amidoaryne Precursors via Ag-Mediated Intramolecular Oxy-Argentation.

An unprecedented silver-mediated intramolecular oxy-argentation of 3-amidoaryne precursors that quickly generates a heteroarylsilver species is developed. AgF acts as both a stoichiometric fluoride source and a reagent for the formation of a benzoxazolylsilver intermediate via aryne generation. Pd-catalyzed coupling reactions of (hetero)aryl iodides with a silver species, generated in situ, allow for the synthesis of various C7-arylated benzoxazoles. As a result, an aryl group is selectively introduced into the meta-position of 3-amidobenzyne precursors. Mechanistic studies have indicated the presence of a benzoxazolylsilver intermediate and revealed that the reaction proceeds via an intramolecular oxy-argentation process, which is initiated by a direct fluoride attack on the silyl group.

Synthesis of Styrenes and E‐Stilbenes by Palladium‐Catalyzed Vinylation of Aryl Iodides with 1,2‐Dibromoethane

AbstractThe Pd‐catalyzed vinylation reactions of aryl iodides using 1,2‐dibromoethane is developed for the synthesis of styrenes and stilbenes. In these reactions, vinyl bromide is generated from 1,2‐dibromoethane and then undergoes reductive cross‐coupling with aryl iodides, affording styrene products. Under slightly modified reaction conditions, styrenes can continue reacting with vinyl bromide to form E‐stilbenes, which provides a one‐pot synthetic method for stilbenes. Alcohols, including iso‐propanol and methanol, are employed as the reductant in these reductive cross‐coupling reactions.

One pot synthesis of carboxylic acid, ester, and amide derivatives from iodoarenes in aqueous solubilized systems using sodium oleate as surfactant at room temperature

Palladium acetate [Pd(OAc)2] catalyzed reaction of aryl iodide utilizing sodium oleate as surfactant was demonstrated in water under ambient temperature and carbon monoxide pressure. Aryl carboxylic acid with different electron withdrawing and donating substituents, and multi-substituted acid derivatives were synthesized in good to excellent isolated yields. Notably, this protocol was also applicable for one pot synthesis of various amide and ester derivatives. Several drug molecules such as niacin, and mefenamic acid alike compound were also obtained in good, isolated yields.