Category: iodides-buliding-blocks

The author of 《Synthesis of γ-Lactones Utilizing Ketoacids and Trimethylsulfoxonium Iodide》 were Triandafillidi, Ierasia; Savvidou, Anatoli; Kokotos, Christoforos G.. And the article was published in Organic Letters in 2019. Reference of Trimethylsulfoxonium iodide The author mentioned the following in the article:

γ-Ketoacids, a δ-ketoacid, and a γ-ketoamide underwent Johnson-Corey-Chaykovsky epoxidation with trimethylsulfoxonium iodide and NaH in DMSO to yield γ-(hydroxymethyl)-γ-lactones, a δ-(hydroxymethyl)-δ-lactone, and a γ-(hydroxymethyl)-γ-lactam in 22-76% yields. The method was used in an attempted synthesis of (+)-asperolide C; (-)-epi-asperolide C was obtained in two steps from (+)-podocarpic acid. The experimental process involved the reaction of Trimethylsulfoxonium iodide(cas: 1774-47-6Reference of Trimethylsulfoxonium iodide)

Trimethylsulfoxonium iodide(cas: 1774-47-6) reacts with sodium hydride to prepare dimethyloxosulfonium methylide, which is used as a methylene-transfer reagent in synthetic chemistry. It is used to prepare ylide, which reacts with carbonyl compounds to get epoxides.Reference of Trimethylsulfoxonium iodide

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

In 2019,Chinese Journal of Chemistry included an article by Zhu, Bo-Han; Wang, Cai-Ming; Su, Hong-Yu; Ye, Long-Wu. Reference of 1-Bromo-4-iodobenzene. The article was titled 《NaBArF4-Catalyzed Oxidative Cyclization of 1,5- and 1,6-Diynes: Efficient and Divergent Synthesis of Functionalized γ- and δ-Lactams》. The information in the text is summarized as follows:

An efficient NaBArF4-catalyzed oxidative cyclization of readily available 1,5- and 1,6-diynes was developed. Importantly, this transition metal-free oxidative catalysis proceeded via a presumable Lewis acid-catalyzed SN2′ pathway, which was distinct from the relevant oxidative rhodium and gold catalysis. This method lead to the facile and practical construction of a diverse range of synthetically useful γ- and δ-lactams in mostly good to excellent yields with broad substrate scope. In the experiment, the researchers used 1-Bromo-4-iodobenzene(cas: 589-87-7Reference of 1-Bromo-4-iodobenzene)

1-Bromo-4-iodobenzene(cas: 589-87-7) has been employed as reagent for in situ desilylation and coupling of silylated alkynes, as starting reagent in the total syntheses of ent-conduramine A and ent-7-deoxypancratistatin (alkaloids), as substrate in copper-free Sonogashira coupling in aqueous acetone in synthesis of β,β,dibromostyrenesReference of 1-Bromo-4-iodobenzene

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

In 2016,Cheung, Chi Wai; Hu, Xile published 《Amine synthesis via iron-catalysed reductive coupling of nitroarenes with alkyl halides》.Nature Communications published the findings.Name: tert-Butyl 4-iodopiperidine-1-carboxylate The information in the text is summarized as follows:

The reductive coupling of nitroarenes RNO2 (R = 4-OHC6H4, OHCH2CH2C6H4, 1-naphthyl, etc.) with alkyl halides R1X (R1 = butan-2-yl, oxolan-3-yl, cyclooctyl, etc.) to yield (hetero)aryl amines, e.g., I has been reported. A simple iron catalyst enables the coupling with numerous primary, secondary and tertiary alkyl halides. Broad scope and high functional group tolerance are demonstrated. Mechanistic study suggests that nitrosoarenes and alkyl radicals are involved as intermediates. This new C-N coupling method provides general and step-economical access to aryl amines. In the experiment, the researchers used tert-Butyl 4-iodopiperidine-1-carboxylate(cas: 301673-14-3Name: tert-Butyl 4-iodopiperidine-1-carboxylate)

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

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

《Structural Analysis and Development of Notum Fragment Screening Hits》 was written by Zhao, Yuguang; Mahy, William; Willis, Nicky J.; Woodward, Hannah L.; Steadman, David; Bayle, Elliott D.; Atkinson, Benjamin N.; Sipthorp, James; Vecchia, Luca; Ruza, Reinis R.; Harlos, Karl; Jeganathan, Fiona; Constantinou, Stefan; Costa, Artur; Kjaer, Svend; Bictash, Magda; Salinas, Patricia C.; Whiting, Paul; Vincent, Jean-Paul; Fish, Paul V.; Jones, E. Yvonne. Safety of 1-Chloro-3-iodobenzeneThis research focused ontriazzole pyrazole benzimidazole synthesis SAR Notum Wnt signaling; Diamond-SGC Poised Library (DSPL); Notum inhibitors; Wnt signaling; fragment screening; hit-to-lead development. The article conveys some information:

The Wnt signaling suppressor Notum is a promising target for osteoporosis, Alzheimer′s disease, and colorectal cancers. To develop novel Notum inhibitors, we used an X-ray crystallog. fragment screen with the Diamond-SGC Poised Library (DSPL) and identified 59 fragment hits from the anal. of 768 data sets. Fifty-eight of the hits were found bound at the enzyme catalytic pocket with potencies ranging from 0.5 to >1000 μM. Anal. of the fragments′ diverse binding modes, enzymic inhibitory activities, and chem. properties led to the selection of six hits for optimization, and five of these resulted in improved Notum inhibitory potencies. One hit, 1-phenyl-1,2,3-triazole 7, and its related cluster members, have shown promising lead-like properties. These became the focus of our fragment development activities, resulting in compound 7d (I)h IC50 0.0067 μM. The large number of Notum fragment structures and their initial optimization provided an important basis for further Notum inhibitor development. In the experimental materials used by the author, we found 1-Chloro-3-iodobenzene(cas: 625-99-0Safety of 1-Chloro-3-iodobenzene)

1-Chloro-3-iodobenzene(cas: 625-99-0) 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. Safety of 1-Chloro-3-iodobenzene Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.

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

Reference of 1-Chloro-3-iodobenzeneIn 2022 ,《Electrochemical Synthesis of Sulfonyl Fluorides with Triethylamine Hydrofluoride》 was published in Chinese Journal of Chemistry. The article was written by Zhang, Lei; Cheng, Xu; Zhou, Qi-Lin. The article contains the following contents:

Hydrofluoride is an industry-preferred fluoride source, and finds extensively application to manufacture diverse fluoro chems. The Et3N-3HF complex is a liquid HF with improve safety. In this work, electrochem. synthesis of a series of sulfonyl fluoride with Et3N-3HF as fluoride source was reported. The sulfinic salt is a smell-less, non-volatile, and air-stable sulfur source in this reaction. With the combination of Et3N-3HF and aryl/alkyl sulfinic salt, the sulfonyl fluorides are achieved without the use of external oxidant. In addition, further advantage in a tandem reaction involving Pd-catalyzed C-S cross-coupling and formation of S-F bond was demonstrated. A variety of functional groups including amino acids, heterocycles, halides are well tolerated. The experimental process involved the reaction of 1-Chloro-3-iodobenzene(cas: 625-99-0Reference of 1-Chloro-3-iodobenzene)

1-Chloro-3-iodobenzene(cas: 625-99-0) belongs to organic iodides. Generally organic iodides can be divided into two classes of alkyl iodides and aryl iodides. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics.Reference of 1-Chloro-3-iodobenzene

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

Computed Properties of C7H7IIn 2019 ,《Stainless steel mesh-GO/Pd NPs: catalytic applications of Suzuki-Miyaura and Stille coupling reactions in eco-friendly media》 was published in Green Chemistry. The article was written by Feizi Mohazzab, Bahareh; Jaleh, Babak; Issaabadi, Zahra; Nasrollahzadeh, Mahmoud; Varma, Rajender S.. The article contains the following contents:

The immobilization of palladium nanoparticles (Pd NPs) on stainless-steel mesh is described in two short steps via deposition of graphene oxide (GO) on the stainless-steel mesh (mesh-GO) by electrophoretic deposition (EPD), preparation of Pd NPs using laser ablation in liquids (LAL) and finally the immobilization of Pd NPs on the mesh-GO by immersion in a Pd NP colloidal solution The novel, efficient and reusable mesh-GO/Pd catalyst was characterized by various techniques such as SEM, EDS, UV-Vis and FT-IR spectroscopy and its catalytic activity was investigated for the Suzuki-Miyaura and Stille coupling reactions in ethanolic water. In the experiment, the researchers used many compounds, for example, 1-Iodo-4-methylbenzene(cas: 624-31-7Computed Properties of C7H7I)

1-Iodo-4-methylbenzene(cas: 624-31-7) is used in wide range of medicals industrial applications as well as in pharmaceutical intermediates, polarizing films for Liquid Crystal Display (LCD) chemicals.Computed Properties of C7H7I

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

In 2015,Fernandez Saez, Nerea; Garcia Lopez, Jesus; Iglesias, Maria Jose; Lopez Ortiz, Fernando published 《Derivatization of (quinolin-8-yl)phosphinimidic amides via ortho-lithiation revisited》.Dalton Transactions published the findings.Formula: C2H4I2 The information in the text is summarized as follows:

The direct ortho-lithiation of N-H containing (quinolin-8-yl)phosphinimidic amides by reaction with 1 equiv of BuLi described by Wang and co-workers was reexamined The multinuclear magnetic resonance (1H, 2H, 7Li, 13C, 15N and 31P) study of the species formed in the monolithiation of N-(tert-butyl)-P,P-diphenyl-N’-(quinolin-8-yl)phosphinimidic amide 5 with BuLi in THF showed that proton abstraction occurred exclusively and quant. at the NH. The combination of the NMR results with a DFT study made it possible to describe the structure of the N-lithiated species 9 as a dimer consisting of an eight-membered ring showing two lithium ions triply coordinated to nitrogen atoms corresponding to the deprotonated amine and aminoquinoline moieties of different monomers. The formation of a polymer featuring the same coordination mode couldn’t be excluded. Optimized conditions for the efficient derivatization of 5 via ortho-lithiation were realized. The reaction of 5 with 2.4 equiv of Me3CLi in THF at -80-25° for 3 h afforded a N,Cortho-dilithiated species that was trapped with electrophiles leading to new functionalized ortho derivatives of 5 in good yields. In addition to this study using 1,2-Diiodoethane, there are many other studies that have used 1,2-Diiodoethane(cas: 624-73-7Formula: C2H4I2) 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.Formula: C2H4I2

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

Bakherad, Mohammad; Keivanloo, Ali; Kalantar, Zahra; Jajarmi, Saeideh published an article on January 12 ,2011. The article was titled 《Pd/C-catalyzed heterocyclization during copper-free Sonogashira coupling: Synthesis of 2-benzylimidazo[1,2-a]pyrimidines in water》, and you may find the article in Tetrahedron Letters.Reference of 1-Chloro-4-iodo-2-nitrobenzene The information in the text is summarized as follows:

An efficient synthesis of 2-benzylimidazo[1,2-a]pyrimidines I (R = 4-O2NC6H4, 3-O2NC6H4, 4-BrC6H4, etc.) in water is accomplished via Pd/C-catalyzed reaction of 2-imino-1-(2-propynyl)pyrimidine with various aryl iodides in the presence of K2CO3 as the base.1-Chloro-4-iodo-2-nitrobenzene(cas: 41252-95-3Reference of 1-Chloro-4-iodo-2-nitrobenzene) was used in this study.

1-Chloro-4-iodo-2-nitrobenzene(cas: 41252-95-3) belongs to organic iodides. Generally organic iodides can be divided into two classes of alkyl iodides and aryl iodides. Reference of 1-Chloro-4-iodo-2-nitrobenzene Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics.

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

Reference of 1-Chloro-4-iodo-2-nitrobenzeneOn June 2, 2008, Bakherad, Mohammad; Nasr-Isfahani, Hossein; Keivanloo, Ali; Doostmohammadi, Nesa published an article in Tetrahedron Letters. The article was 《Pd-Cu catalyzed heterocyclization during Sonogashira coupling: synthesis of 2-benzylimidazo[1,2-a]pyridine》. The article mentions the following:

The reaction of 2-amino-1-(2-propynyl)pyridinium bromide with various iodobenzenes, catalyzed by Pd-Cu, leads to the formation of 2-benzylimidazo[1,2-a]pyridines. In the part of experimental materials, we found many familiar compounds, such as 1-Chloro-4-iodo-2-nitrobenzene(cas: 41252-95-3Reference of 1-Chloro-4-iodo-2-nitrobenzene)

1-Chloro-4-iodo-2-nitrobenzene(cas: 41252-95-3) belongs to 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.Reference of 1-Chloro-4-iodo-2-nitrobenzene

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

Name: 1-Chloro-4-iodo-2-nitrobenzeneOn October 20, 2008 ,《Synthesis of 2-benzylimidazo[2,1-b][1,3]benzothiazoles through palladium-catalyzed heteroannulation of acetylenic compounds》 was published in Tetrahedron Letters. The article was written by Bakherad, Mohammad; Nasr-Isfahani, Hossein; Keivanloo, Ali; Sang, Golnaz. The article contains the following contents:

Reactions of 2-imino-3-(2-propynyl)-1,3-benzothiazole with electron-deficient iodobenzenes RI (R = 2-O2NC6H4, 3-O2NC6H4, 4-O2NC6H4, 2-Me-4-O2NC6H3, 2-O2N-4-ClC6H3, 2-Cl-4-O2NC6H3, 3-O2N-4-ClC6H3, 4-NCC6H4, 4-MeO2CC6H4) in the presence of bis(triphenylphosphine)palladium dichloride leads to 2-benzylimidazo[2,1-b][1,3]benzothiazoles I in 55-87% yields. The results came from multiple reactions, including the reaction of 1-Chloro-4-iodo-2-nitrobenzene(cas: 41252-95-3Name: 1-Chloro-4-iodo-2-nitrobenzene)

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. Name: 1-Chloro-4-iodo-2-nitrobenzene Organic iodides can be alkyl, alkenyl, or alkynyl, and all of them are very reactive toward with many kinds of nucleophiles.

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