Tag: 200-300

In 2015,Zirakzadeh, Afrooz; Herlein, Alexander; Gross, Manuela A.; Mereiter, Kurt; Wang, Yaping; Weissensteiner, Walter published 《Halide-Mediated Ortho-Deprotonation Reactions Applied to the Synthesis of 1,2- and 1,3-Disubstituted Ferrocene Derivatives》.Organometallics published the findings.Name: 1,2-Diiodoethane The information in the text is summarized as follows:

The ortho-deprotonation of halide-substituted ferrocenes by treatment with lithium tetramethylpiperidide (LiTMP) has been investigated. Iodo-, bromo-, and chloro-substituted ferrocenes were easily deprotonated adjacent to the halide substituents. The synthetic applicability of this reaction was, however, limited by the fact that, depending on the temperature and the degree of halide substitution, scrambling of both iodo and bromo substituents at the ferrocene core took place. Iodoferrocenes could not be transformed selectively into ortho-substituted iodoferrocenes since, in the presence of LiTMP, the iodo substituents scrambled efficiently even at -78°, and this process had occurred before electrophiles had been added. Bromoferrocene and certain monobromo-substituted derivatives, however, could be efficiently ortho-deprotonated at low temperature and reacted with a number of electrophiles to afford 1,2- and 1,2,3-substituted ferrocene derivatives For example, 2-bromo-1-iodoferrocene was synthesized by ortho-deprotonation of bromoferrocene and reaction with the electrophiles diiodoethane and diiodotetrafluoroethane, resp. In this and related cases the iodide scrambling process and further product deprotonation due to the excess LiTMP could be suppressed efficiently by running the reaction at low temperature and in inverse mode. In contrast to the low-temperature process, at room temperature bromo substituents in bromoferrocenes scrambled in the presence of LiTMP. Chloro- and 1,2-dichloroferrocene could be ortho-deprotonated selectively, but in neither case was scrambling of a chloro substituent observed As a further application of this ortho-deprotonation reaction, a route for the synthesis of 1,3-disubstituted ferrocenes was developed. 1,3-Diiodoferrocene was accessible from bromoferrocene in four steps. On a multigram scale an overall yield of 41% was achieved. 1,3-Diiodoferrocene was further transformed into sym. 1,3-disubstituted ferrocenes (1,3-R2Fc; R = CHO, COOEt, CN, CH:CH2).1,2-Diiodoethane(cas: 624-73-7Name: 1,2-Diiodoethane) was used in this study.

1,2-Diiodoethane(cas: 624-73-7) is one of organic iodides. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond. Iodo alkanes participate in a variety of organic synthesis reactions, which include the Simmons–Smith reaction (cyclopropanation using iodomethane), Williamson ether synthesis, Wittig reaction, Grignard reaction, alkyl coupling reactions, and Wurtz reaction.Name: 1,2-Diiodoethane

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

《The invention of radical reactions. Part XVI. Radical decarboxylative bromination and iodination of aromatic acids》 was published in Tetrahedron in 1987. These research results belong to Barton, Derek H. R.; Lacher, Brigitte; Zard, Samir Z.. Category: iodides-buliding-blocks The article mentions the following:

Thiohydroxamic esters of aromatic carboxylic acids undergo clean decarboxylative bromination or iodination on treatment with bromotrichloromethane, iodoform, or diiodomethane in the presence of a radical initiator. E.g., reaction of 1-naphthoyl chloride with the Na salt of N-hydroxypyridine-2-thione and BrCCl3 in o-Cl2C6H4 in the presence of AIBN gave 82% 1-bromonaphthalene. In addition to this study using 1-Chloro-4-iodo-2-nitrobenzene, there are many other studies that have used 1-Chloro-4-iodo-2-nitrobenzene(cas: 41252-95-3Category: iodides-buliding-blocks) was used in this study.

1-Chloro-4-iodo-2-nitrobenzene(cas: 41252-95-3) belongs to organic iodides. The carbon-iodine bond is weaker than other carbon-halogen bonds due to the poor electronegative nature of the iodine atom. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.Category: iodides-buliding-blocks

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

SDS of cas: 589-87-7In 2019 ,《One-Pot Electrochemical Nickel-Catalyzed Decarboxylative Sp2-Sp3 Cross-Coupling》 was published in Organic Letters. The article was written by Koyanagi, Takaoki; Herath, Ananda; Chong, Ashley; Ratnikov, Maxim; Valiere, Andrew; Chang, Jim; Molteni, Valentina; Loren, Jon. The article contains the following contents:

A one-pot electrochem. nickel-catalyzed decarboxylative sp2-sp3 cross-coupling reaction has been developed using redox-active esters prepared in situ from alkyl carboxylates and N-hydroxyphthalimide tetramethyluronium hexafluorophosphate (PITU). This undivided cell one-pot method enables C-C bond formation using inexpensive, benchtop-stable reagents with isolated yields up to 95% with good functional group tolerance, which includes nitrile, ketone, ester, alkene and selectivity over other aromatic halogens. The experimental part of the paper was very detailed, including the reaction process of 1-Bromo-4-iodobenzene(cas: 589-87-7SDS of cas: 589-87-7)

1-Bromo-4-iodobenzene(cas: 589-87-7) is mainly used as the OLED pharmaceutical intermediate, as reagent for in situ desilylation and coupling of silylated alkynes, as substrate in copper-free Sonogashira coupling in aqueous acetone..SDS of cas: 589-87-7 It is also used in synthesis of β,β,dibromostyrenes, as starting reagent in the total syntheses of ent-conduramine A and ent-7-deoxypancratistatin (alkaloids)

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Formula: C2H4I2In 2015 ,《1,3,5-[(tBu2MeSi)2Si]3C6H3: isolable Si-centered triradical with a high-spin quartet ground state》 was published in Chemistry Letters. The article was written by Nozawa, Takeshi; Ichinohe, Masaaki; Sekiguchi, Akira. The article contains the following contents:

Reductive deiodination of 1,3,5-tris[2,2-di-tert-butyl-1-(di-tert-butylmethylsilyl)-1-iodo-2-methyldisilanyl]benzene (1) with KC8 results in the formation of isolable Si-centered triradical 1,3,5-[(t-Bu2MeSi)2Si]3C6H3 (2), which was characterized by x-ray crystallog. and ESR (EPR) spectroscopy. The quartet ground state for triradical 2 was established using EPR spectroscopy by Curie plots (5-60 K) for the characteristic Δm = 2 and Δm = 3 transitions. The experimental process involved the reaction of 1,2-Diiodoethane(cas: 624-73-7Formula: C2H4I2)

1,2-Diiodoethane(cas: 624-73-7) is one of organic iodides. The carbon-iodine bond is weaker than other carbon-halogen bonds due to the poor electronegative nature of the iodine atom. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine. Organic iodides can be alkyl, alkenyl, or alkynyl, and all of them are very reactive toward with many kinds of nucleophiles.Formula: C2H4I2

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Formula: C5H4INIn 2022 ,《Pyridine-Containing Donor-Acceptor Diarylnitroxides: Noncovalent Stabilization of the Redox States》 appeared in ChemPlusChem. The author of the article were Levitskiy, Oleg A.; Bogdanov, Alexey V.; Klimchuk, Ivan A.; Magdesieva, Tatiana V.. The article conveys some information:

A series of new pyridyl- or 2-pyridyloxide-containing donor-acceptor diarylnitroxides was obtained and characterized; high stability of the ortho-2-pyridyl-containing diarylnitroxides was determined by kinetic measurements (τ1/2=1733 h in benzene). Comparative voltammetric study of new nitroxides and their analog in which the Py replaces the Ph group revealed both through-bond and through-space stabilization of the NO redox states with the pyridyl/ 2-pyridyloxide moiety, providing reversibility of both oxidation and reduction processes. Adaptive conformational behavior of new pyridyl/pyridyloxide containing nitroxides upon one-electron oxidation and reduction was confirmed by DFT calculations Stimuli-responsive conformational changes allow switching on/off dispersion and electrostatic interactions within the mol. and increase stability of the redox states. Spectroelectrochem. measurements provided exptl. evidence for reversibility of the through-space stabilization of the oxidized state of the nitroxides with the neighboring pyridine lone pair. In the experiment, the researchers used 4-Iodopyridine(cas: 15854-87-2Formula: C5H4IN)

4-Iodopyridine(cas: 15854-87-2) is a halogenated heterocycle that is a building block for proteomics research. 4-Iodopyridine is used as a reagent in the synthesis of indazolylamides as glucocorticoid receptor agonists.Formula: C5H4IN

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

In 2022,Zhao, Fen; Abdellaoui, Mehdi; Hagui, Wided; Ballarin-Marion, Maria; Berthet, Jerome; Corce, Vincent; Delbaere, Stephanie; Dossmann, Heloise; Espagne, Agathe; Forte, Jeremy; Jullien, Ludovic; Le Saux, Thomas; Mouries-Mansuy, Virginie; Ollivier, Cyril; Fensterbank, Louis published an article in Nature Communications. The title of the article was 《Reactant-induced photoactivation of in-situ generated organogold intermediates leading to alkynylated indoles via Csp2-Csp cross-coupling》.Formula: C6H5ClIN The author mentioned the following in the article:

In this context, an access to 2,3-disubstituted indoles from o-alkynyl aniline and iodoalkyne derivatives via a gold-catalyzed sequence under visible-light irradiation and in the absence of an exogenous photocatalyst was uncovered. A wide scope of the process was observed Of note, 2-iodo-ynamides was used as electrophiles in this cross-coupling reaction. The resulting N-alkynyl indoles lend themselves to post-functionalization affording valuable scaffolds, notably benzo[a]carbazoles. Mechanistic studies converge on the fact that a potassium sulfonyl amide generates emissive aggregates in the reaction medium. Static quenching of these aggregates by a vinylgold(I) intermediate yields to an excited state of the latter, which can react with an electrophile via oxidative addition and reductive elimination to forge the key C-C bond. This reactant-induced photoactivation of an organogold intermediate opens rich perspectives in the field of cross-coupling reactions.4-Chloro-2-iodoaniline(cas: 63069-48-7Formula: C6H5ClIN) was used in this study.

4-Chloro-2-iodoaniline(cas: 63069-48-7) belongs to anime. The reaction of alkyl halides, R―X, where X is a halogen, or analogous reagents with ammonia (or amines) is useful with certain compounds. Not all alkyl halides are effective reagents; the reaction is sluggish with secondary alkyl groups and fails with tertiary ones. Its usefulness is largely confined to primary alkyl halides (those having two hydrogen atoms on the reacting site).Formula: C6H5ClIN

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

In 2022,Ren, Jing; Jia, Meng-Cheng; Du, Feng-Huan; Zhang, Chi published an article in Chinese Chemical Letters. The title of the article was 《A general method for one-step synthesis of monofluoroiodane(III) reagents using silver difluoride》.Safety of 2-Iodobenzoic acid The author mentioned the following in the article:

A new general method for one-step synthesis of four kinds of fluoroiodane(III) reagents by treating the corresponding aryl iodides with silver difluoride (AgF2) was reported. This is the first method applicable for the synthesis of all four fluoroiodane(III) reagents including p-iodotoluene difluoride, fluoro-benziodoxoles, fluoro-benziodoxolones and fluoro-N-acetylbenziodazole. AgF2 was firstly employed in the direct oxidative fluorination of iodobenzene and thus has shown its outstanding oxidation and fluorine-transfer ability. The use of AgF2 has improved the synthesis of fluoroiodane(III) reagents by shortening the reaction steps, avoiding the use of hazardous reagents and simplifying the exptl. operations. It was worth noting that the developed first one-step direct synthetic method for fluoro-benziodoxolones, while fluoro-benziodoxolones can only be synthesized through Cl→F ligand exchange reaction previously. In the experimental materials used by the author, we found 2-Iodobenzoic acid(cas: 88-67-5Safety of 2-Iodobenzoic acid)

2-Iodobenzoic acid(cas: 88-67-5) belongs to organic iodides. The carbon-iodine bond is weaker than other carbon-halogen bonds due to the poor electronegative nature of the iodine atom. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.Safety of 2-Iodobenzoic acid

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

In 2022,Xu, Chen; Yin, Chenjia; Wu, Wenjun; Ma, Xiang published an article in Science China: Chemistry. The title of the article was 《Tunable room-temperature phosphorescence and circularly polarized luminescence encoding helical supramolecular polymer》.Reference of 1-Bromo-4-iodobenzene The author mentioned the following in the article:

Supramol. polymers with different functionalities have been continuously developed in the past decade because of their indispensable role in soft materials. However, pure organic supramol. polymers with stable room temperature phosphorescence (RTP) emission were very rarely reported for the difficulties of synthesis and achieving RTP in solution Herein, soluble helical supramol. polymers with circularly polarized room-temperature phosphorescence were developed via a facile host-guest strategy. Through assembly, a transition from pure fluorescence to almost pure RTP emission was achieved. Adjusting the asymmetry of guest could easily control the chiroptical property of supramol. polymers. This work provides new opportunities for the design and development of intelligent soft functional soft materials. [graphic not available: see fulltext] In addition to this study using 1-Bromo-4-iodobenzene, there are many other studies that have used 1-Bromo-4-iodobenzene(cas: 589-87-7Reference of 1-Bromo-4-iodobenzene) was used in this study.

1-Bromo-4-iodobenzene(cas: 589-87-7) is mainly used as the OLED pharmaceutical intermediate, as reagent for in situ desilylation and coupling of silylated alkynes, as substrate in copper-free Sonogashira coupling in aqueous acetone..Reference of 1-Bromo-4-iodobenzene It is also used in synthesis of β,β,dibromostyrenes, as starting reagent in the total syntheses of ent-conduramine A and ent-7-deoxypancratistatin (alkaloids)

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Pei, Xiaoyan; Xiang, Deng; Luo, Zhengxiu; Lei, Fukun; Guo, Zhanglong; Liu, Dong; Zhao, Zhigang; Ran, Maofei; Dai, Tao published an article in 2021. The article was titled 《Catalytic performance of palladium nanoparticles encapsulated within nitrogen-doped carbon during Heck reaction》, and you may find the article in Journal of Catalysis.Application In Synthesis of 1-Bromo-4-iodobenzene The information in the text is summarized as follows:

The Confinement effect is an effective strategy for enhancing the performance of catalysts during various reactions. We developed a strategy to encapsulating Palladium nanoparticles with a dopamine-derived N-doped multilayer carbon shell to catalyze the Heck reaction between iodobenzene and carbon-carbon double-bond compounds (styrene and Me acrylate). The catalytic performances of Pd nanoparticles encapsulated within a N-doped carbon layer (Pd@N-C) and those attached to the external surface of such a layer (Pd/N-C) were evaluated and compared. Pd@N-C exhibited a lower reaction activation energy (78 kJ/mol) than that of Pd/N-C (106 kJ/mol). Thus, the activity of Pd@N-C during the Heck reaction between iodobenzene and Me acrylate was approx. 20 times higher than that of Pd/N-C-200. The results of thermal filtration and recycling tests indicated that Pd@N-C showed a lower degree of leaching than that of Pd/N-C-200 owing to the spatial restriction effect of the cavity in the case of the former. Hence, the superior catalytic performance of Pd@N-C can be ascribed to the confinement of the Pd nanoparticles within the N-doped carbon layer. Finally, we useCinnamatesd these catalysts to synthesize a range of para-substituted iodobenzene derivatives, thus demonstrating the potential of Pd-encapsulating catalysts for use in the Heck reaction on the tech. scale. The experimental part of the paper was very detailed, including the reaction process of 1-Bromo-4-iodobenzene(cas: 589-87-7Application In Synthesis of 1-Bromo-4-iodobenzene)

1-Bromo-4-iodobenzene(cas: 589-87-7) is mainly used as the OLED pharmaceutical intermediate, as reagent for in situ desilylation and coupling of silylated alkynes, as substrate in copper-free Sonogashira coupling in aqueous acetone..Application In Synthesis of 1-Bromo-4-iodobenzene It is also used in synthesis of β,β,dibromostyrenes, as starting reagent in the total syntheses of ent-conduramine A and ent-7-deoxypancratistatin (alkaloids)

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Cheng, Yaohang; Yu, Shijie; He, Yuhang; An, Guanghui; Li, Guangming; Yang, Zhenyu published an article in 2021. The article was titled 《C4-arylation and domino C4-arylation/3,2-carbonyl migration of indoles by tuning Pd catalytic modes: Pd(I)-Pd(II) catalysis vs. Pd(II) catalysis》, and you may find the article in Chemical Science.Application In Synthesis of 4-Iodobenzaldehyde The information in the text is summarized as follows:

Efficient C4-arylation and domino C4-arylation/3,2-carbonyl migration of indoles was developed. The former route enables C4-arylation in a highly efficient and mild manner and the latter route provides an alternative straightforward protocol for synthesis of C2/C4 disubstituted indoles. The mechanism studies imply that the different reaction pathways were tuned by the distinct acid additives, which led to either the Pd(I)-Pd(II) pathway or Pd(II) catalysis. In the experiment, the researchers used many compounds, for example, 4-Iodobenzaldehyde(cas: 15164-44-0Application In Synthesis of 4-Iodobenzaldehyde)

4-Iodobenzaldehyde(cas: 15164-44-0) is used in synthesis of 4-[2-(trimethylsilyl)ethynyl]benzaldehyde, 5,15-dimesityl-10-(3-[2-(trimethylsilyl)ethynyi]phenyl}-20-(4-iodophenyl)porphyrin, and 5,15-dimesityl-10-[3,5-bis{2-[4-(N,N’-difluoroboryl-1,9-dimethyidipyrrin-5-yl)-phenyl]ethynyl}phenyl]-20-(4-iodophenyl)porphyrin.Application In Synthesis of 4-Iodobenzaldehyde

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com