Month: October 2022

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

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

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

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

Category: iodides-buliding-blocksIn 2016 ,《Reaction of Alkyl Halides with Rongalite: One-Pot and Telescoped Syntheses of Aliphatic Sulfonamides, Sulfonyl Fluorides, and Unsymmetrical Sulfones》 was published in Organic Letters. The article was written by Shavnya, Andre; Coffey, Steven B.; Hesp, Kevin D.; Ross, Stuart C.; Tsai, Andy S.. The article contains the following contents:

An efficient methodol. has been developed for the one-pot or telescoped synthesis of aliphatic sulfonamides, sulfonyl fluorides, and unsym. sulfones on the basis of interrupted alkylation of sodium hydroxymethylsulfinate (rongalite) with alkyl halides. The protocols are conducted under mild conditions, use inexpensive and shelf-stable reagents, and are not sensitive to air/moisture. These conditions can be applied in rapid parallel chem. synthesis, which was demonstrated by the preparation of a small sulfonamide library based on the core structure of the anticoagulant drug Tirofiban. The experimental process involved the reaction of tert-Butyl 4-iodopiperidine-1-carboxylate(cas: 301673-14-3Category: iodides-buliding-blocks)

tert-Butyl 4-iodopiperidine-1-carboxylate(cas: 301673-14-3) 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.Category: iodides-buliding-blocks

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

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

In 2016,Sembera, Filip; Plutnar, Jan; Higelin, Alexander; Janousek, Zbynek; Cisarova, Ivana; Michl, Josef published 《Metal Complexes with Very Large Dipole Moments: the Anionic Carborane Nitriles 12-NC-CB11X11- (X = H, F, CH3) as Ligands on Pt(II) and Pd(II)》.Inorganic Chemistry published the findings.SDS of cas: 624-73-7 The information in the text is summarized as follows:

The anionic nitriles 1-R-12-NC-CB11H10- (R = H, CH3, I, COOH), 12-NC-1-H-CB11Me10-, and 12-NC-1-H-CB11F10- were prepared, and three of them were examined for complex formation with (Et3P)2Pt(II) and (Et3P)2Pd(II). Several stable internally charge-compensated zwitterionic complexes were obtained and characterized. RI-BP86/SV(P) calculations suggest that their dipole moments exceed 20 D. An attempt to measure the dipole moments in solution failed due to insufficient solubility in solvents of low polarity.1,2-Diiodoethane(cas: 624-73-7SDS of cas: 624-73-7) was used in this study.

1,2-Diiodoethane(cas: 624-73-7) is one of organic iodides. Organic iodides are used in veterinary products (Organic Iodide Powder) as a nutritional source of iodine. In the chemical industry, alkyl iodides serve as excellent alkylating agents and, specifically, methyl iodide is used as a methylating agent in the synthesis of various pharmaceutical drugs. Oceanic alkyl iodides are believed to be the principal source of atmospheric iodine.SDS of cas: 624-73-7

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

In 2018,Hofmayer, Maximilian S.; Hammann, Jeffrey M.; Cahiez, Gerard; Knochel, Paul published 《Iron-Catalyzed C(sp2)-C(sp3) Cross-Coupling Reactions of Di(hetero)arylmanganese Reagents and Primary and Secondary Alkyl Halides》.Synlett published the findings.SDS of cas: 301673-14-3 The information in the text is summarized as follows:

An iron-catalyzed cross-coupling between di(hetero)arylmanganese reagents and primary and secondary alkyl halides is reported. No rearrangement of secondary alkyl halides to unbranched products was observed in these C-C bond-forming reactions. In addition to this study using tert-Butyl 4-iodopiperidine-1-carboxylate, there are many other studies that have used tert-Butyl 4-iodopiperidine-1-carboxylate(cas: 301673-14-3SDS of cas: 301673-14-3) was used in this study.

tert-Butyl 4-iodopiperidine-1-carboxylate(cas: 301673-14-3) 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.SDS of cas: 301673-14-3

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

In 2019,Dalton Transactions included an article by Kikukawa, Yuji; Kitajima, Hiromasa; Hayashi, Yoshihito. Application of 624-73-7. The article was titled 《Evaluation of the chemo- and shape-selective association of a bowl-type dodecavanadate cage with an electron-rich group》. The information in the text is summarized as follows:

The host-guest interaction between a half spherical-type dodecavanadate (V12) and a neutral mol. guest was evaluated by monitoring the flip of a VO5 unit caused by the presence or absence of a guest in the cavity of V12. In N,N-dimethylformamide (DMF), V12 adopted the guest-free form (V12-free). By the addition of several guest mols., such as acetonitrile, nitromethane, and dichloromethane, the structural conversion to the guest-inserted form (V12(guest)) was observed with the affinity constants of 137 ± 10 M-1, 0.14 ± 0.1 M-1, and 0.15 ± 0.1 M-1, resp. In the case of 1,2-dichloroethane, 1,2-dibromoethane, and 1,2-diiodoethane, the constants were 35 ± 5 M-1, 114 ± 5 M-1, and 2.1 ± 0.5 M-1, resp., suggesting that the bromo group is the best fit to the cavity of the bowl. A cyclic carbonate, 5- and 6-membered lactones, cyclobutanone, and hexanal were inserted into the V12 host, while a non-cyclic carbonate, non-cyclic and 7-membered cyclic ester, a ketone with a 5-membered ring, and benzaldehyde showed no effect on the guest insertion. The V12 host preferred to hold a guest with an electron-rich group, and the bowl-type structure showed the unique shape-selective interaction with the guest. The results came from multiple reactions, including the reaction of 1,2-Diiodoethane(cas: 624-73-7Application of 624-73-7)

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.Application of 624-73-7

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