Category: iodides-buliding-blocks

In 2022,Wu, Yu; Wu, Feng-Wei; Zhou, Kun; Li, Yiming; Chen, Lei; Wang, Shuang; Xu, Zhen-Yuan; Lou, Shao-Jie; Xu, Dan-Qian published an article in Chemical Communications (Cambridge, United Kingdom). The title of the article was 《Rapid access to 9-arylfluorenes and spirobifluorenes through Pd-catalyzed C-H arylation/deaminative annulation》.Recommanded Product: 1-Bromo-3-iodobenzene The author mentioned the following in the article:

Herein, a facile synthesis of 9-arylfluorenes and spirobifluorenes from readily available 1,1-diarylmethylamines and iodoarenes through Pd-cataylzed C(sp2)-H arylation and a sequential deaminative annulation is reported. The reaction features high efficiency and simplicity of operation, constituting an interesting shortcut to access fluorene compounds In the experimental materials used by the author, we found 1-Bromo-3-iodobenzene(cas: 591-18-4Recommanded Product: 1-Bromo-3-iodobenzene)

1-Bromo-3-iodobenzene(cas: 591-18-4) has been used in the preparation of 1-(3′-bromophenyl)-3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodec-1-ene and 1-(3′-bromophenyl)-3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooct-1-ene.Recommanded Product: 1-Bromo-3-iodobenzene Further, it is involved in the preparation of oxygen-tethered 1,6-enynes.

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

Andreev, Ivan A.; Ratmanova, Nina K.; Augustin, Andre U.; Ivanova, Olga A.; Levina, Irina I.; Khrustalev, Victor N.; Werz, Daniel B.; Trushkov, Igor V. published an article in 2021. The article was titled 《Protic Ionic Liquid as Reagent, Catalyst, and Solvent: 1-Methylimidazolium Thiocyanate》, and you may find the article in Angewandte Chemie, International Edition.Recommanded Product: Trimethylsulfoxonium iodide The information in the text is summarized as follows:

We propose a new concept of the triple role of protic ionic liquids with nucleophilic anions: (a) a regenerable solvent, (b) a Broensted acid inducing diverse transformations via general acid catalysis, and (c) a source of a nucleophile. The efficiency of this strategy was demonstrated using thiocyanate-based protic ionic liquids for the ring-opening of donor-acceptor cyclopropanes. A wide variety of activated cyclopropanes were found to react with 1-methylimidazolium thiocyanate under mild metal-free conditions via unusual nitrogen attack of the ambident thiocyanate ion on the electrophilic center of the three-membered ring affording pyrrolidine-2-thiones bearing donor and acceptor substituents at the C(5) and C(3) atoms, resp., in a single time-efficient step [e.g., I → II (81%)]. The ability of 1-methylimidazolium thiocyanate to serve as a triplex reagent was exemplarily illustrated by (4+2)-annulation with 1-acyl-2-(2-hydroxyphenyl)cyclopropane, epoxide ring-opening and other organic transformations. Safety: ammonia evolution in cation metathesis reactions → carry out in fume hood. After reading the article, we found that the author used Trimethylsulfoxonium iodide(cas: 1774-47-6Recommanded Product: 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. Further, it reacts with alfa,beta-unsaturated esters to get cyclopropyl esters.Recommanded Product: Trimethylsulfoxonium iodide

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

Ghosh, Prithwish; Kwon, Na Yeon; Kim, Saegun; Han, Sangil; Lee, Suk Hun; An, Won; Mishra, Neeraj Kumar; Han, Soo Bong; Kim, In Su published an article in 2021. The article was titled 《C-H Methylation of Iminoamido Heterocycles with Sulfur Ylides》, and you may find the article in Angewandte Chemie, International Edition.Synthetic Route of C3H9IOS The information in the text is summarized as follows:

The direct methylation of N-heterocycles is an important transformation for the advancement of pharmaceuticals, agrochems., functional materials, and other chem. entities. Herein, the unprecedented C(sp2)-H methylation of iminoamido heterocycles as nucleoside base analogs is described. Notably, trimethylsulfoxonium salt was employed as a methylating agent under aqueous conditions. A wide substrate scope and excellent level of functional-group tolerance were attained. Moreover, this method can be readily applied to the site-selective methylation of azauracil nucleosides. The feasibility of gram-scale reactions and various transformations of the products highlight the synthetic potential of the developed method. Combined deuterium-labeling experiments aided the elucidation of a plausible reaction mechanism. Thus, e.g., treatment of pyrazinone I with trimethylsulfoxonium iodide and KOH in H2O afforded II (91%). In the experimental materials used by the author, we found Trimethylsulfoxonium iodide(cas: 1774-47-6Synthetic Route of C3H9IOS)

Trimethylsulfoxonium iodide(cas: 1774-47-6) is a sulfoxonium salt. It is used to generate dimethyloxosulfonium methylide by reaction with sodium hydride. The latter compound is used as a methylene-transfer reagent, and is used to prepare epoxides.Synthetic Route of C3H9IOS

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

Cadge, Jamie A.; Bower, John F.; Russell, Christopher A. published their research in Angewandte Chemie, International Edition in 2021. The article was titled 《A Systematic Study of the Effects of Complex Structure on Aryl Iodide Oxidative Addition at Bipyridyl-Ligated Gold(I) Centers》.HPLC of Formula: 15164-44-0 The article contains the following contents:

A combined theor. and exptl. approach was used to study the unusual mechanism of oxidative addition of aryl iodides to [bipyAu(C2H4)]+ complexes. The modular nature of this system allowed a systematic assessment of the effects of complex structure. Computational comparisons between cationic Au and the isolobal (neutral) Pd0 and Pt0 complexes revealed similar mechanistic features, but with oxidative addition being significantly favored for the group 10 metals. Further differences between Au and Pd were seen in exptl. studies: studying reaction rates as a function of electronic and steric properties showed that ligands bearing more electron-poor functionality increase the rate of oxidative addition; in a complementary way, electron-rich aryl iodides give faster rates. This divergence in mechanism compared to Pd suggests that Ar-X oxidative addition with Au can underpin a broad range of new or complementary transformations. In the experiment, the researchers used 4-Iodobenzaldehyde(cas: 15164-44-0HPLC of Formula: 15164-44-0)

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.HPLC of Formula: 15164-44-0

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

《Synthesis and characterization of nitro-functionalized hydroxyl-terminated polybutadiene using N-iodosuccinimide》 was written by Ghayeni, Hamid Reza; Razeghi, Reza; Olyaei, Abolfazl. Product Details of 516-12-1 And the article was included in Polymer Bulletin (Heidelberg, Germany) in 2020. The article conveys some information:

A convenient, inexpensive and highly efficient one-pot procedure of synthesizing nitro-functionalized hydroxyl-terminated polybutadiene (Nitro-HTPB) is reported by the reaction of hydroxyl-terminated polybutadiene (HTPB) and sodium nitrite in the presence of N-iodosuccinimide in EG-EtOAc-H2O at 60°C for 24 h. The investigation of the effective parameters on the synthesis of Nitro-HTPB such as amounts of reactants, temperature and reaction time indicated that in the optimum reaction conditions, the nitration HTPB backbone is restricted to 6.7% of double bonds until the outstanding phys. and chem. properties of HTPB are retained. The Nitro-HTPB was characterized by FTIR, 1H NMR, 13C NMR, DSC and TGA. The polymer showed good thermal stability, yield of 93%, viscosity of 14.2 Pa.s-1, number average mol. weight of 2730 gmol-1 and hydroxyl value of 34 mg KOH per g. After reading the article, we found that the author used 1-Iodopyrrolidine-2,5-dione(cas: 516-12-1Product Details of 516-12-1)

1-Iodopyrrolidine-2,5-dione(cas: 516-12-1) is used in the preparation of vinyl sulfones from olefins and benzenesulfinic acid. It acts as a source for I+ and involved in Hunsdiecker reactions for the conversion of cinnamic acids, and propiolic acids to the corresponding alfa-halostyrenes and 1-halo-1-alkynes respectively. Product Details of 516-12-1

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

《Enantioselective Total Synthesis of Cotylenin A》 was written by Uwamori, Masahiro; Osada, Ryunosuke; Sugiyama, Ryoji; Nagatani, Kotaro; Nakada, Masahisa. Category: iodides-buliding-blocks And the article was included in Journal of the American Chemical Society in 2020. The article conveys some information:

A convergent enantioselective total synthesis of cotylenin A is described. The A-ring fragment, prepared via the catalytic asym. intramol. cyclopropanation developed in our laboratory, and the C-ring fragment, prepared from a known chiral compound via a modified acyl radical cyclization, were successfully assembled by the Utimoto coupling reaction. The formidable carbocyclic eight-membered ring of cotylenin A was efficiently constructed by a palladium-mediated cyclization. All the hydroxy groups in the scaffold were stereoselectively introduced, and a modified reducing reagent, Me4NBH(O2CiPr)3, has been developed. The sugar moiety fragment was prepared via three consecutive carbon-oxygen bond-forming reactions, and the glycosylation was accomplished using Wan’s protocol. In the part of experimental materials, we found many familiar compounds, such as 1,2-Diiodoethane(cas: 624-73-7Category: iodides-buliding-blocks)

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.Category: iodides-buliding-blocks

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

In 2022,Salardon, Noemi; Otarola, Guillermo; Manas, Clara; Merino, Estibaliz; Batanero, Belen published an article in Journal of Environmental Chemical Engineering. The title of the article was 《Electrochemically driven one-pot oxidative conversion of arylhydrazines into aromatic iodides》.SDS of cas: 90-14-2 The author mentioned the following in the article:

The efficient metal-free electrosynthesis of aryl iodides ArI [Ar = Ph, 4-OMeC6H4, 1-naphthyl, etc.] was here reported starting from aryl hydrazines. Surprisingly this dinitrated arylhydrazine minimized, under the applied exptl. conditions, any anodic multilayered film formation. This sustainable iodide-mediated oxidative dehydrazination enabled coupling reaction of electrogenerated iodine with aryl radicals from electron-deficient arylhydrazines employing electricity as the driving force and an inexpensive halogen source. A mechanistic proposal explaining the formation of aryl iodides was presented and discussed. In the part of experimental materials, we found many familiar compounds, such as 1-Iodonaphthalene(cas: 90-14-2SDS of cas: 90-14-2)

1-Iodonaphthalene(cas: 90-14-2) 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: 90-14-2

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

Rezayee, Nomaan M.; Enemaerke, Valdemar J.; Linde, Sif T.; Lamhauge, Johannes N.; Reyes-Rodriguez, Gabriel J.; Joergensen, Karl Anker; Lu, Chenxi; Houk, K. N. published their research in Journal of the American Chemical Society in 2021. The article was titled 《An Asymmetric SN2 Dynamic Kinetic Resolution》.Category: iodides-buliding-blocks The article contains the following contents:

The SN2 reaction exhibits the classic Walden inversion, indicative of the stereospecific backside attack of the nucleophile on the stereogenic center. Observation of the inversion of the stereocenter provides evidence for an SN2-type displacement. However, this maxim is contingent on substitution proceeding on a discrete stereocenter. Here we report an SN2 reaction that leads to enantioenrichment of product despite starting from a racemic mixture of starting material. The enantioconvergent reaction proceeds through a dynamic Walden cycle, involving an equilibrating mixture of enantiomers, initiated by a chiral aminocatalyst and terminated by a stereoselective SN2 reaction at a tertiary carbon to provide a quaternary carbon stereocenter. A combination of computational, kinetic, and empirical studies elucidates the multifaceted role of the chiral organocatalyst to provide a model example of the Curtin-Hammett principle. These examples challenge the notion of enantioenriched products exclusively arising from predefined stereocenters when operating through an SN2 mechanism. Based on these principles, examples are included to highlight the generality of the mechanism. We anticipate the asym. SN2 dynamic kinetic resolution to be used for a variety of future reactions. The experimental part of the paper was very detailed, including the reaction process of Trimethylsulfoxonium iodide(cas: 1774-47-6Category: iodides-buliding-blocks)

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.Category: iodides-buliding-blocks

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

《A Macrocycle Based on a Heptagon-Containing Hexa-peri-hexabenzocoronene》 was written by Jimenez, Vicente G.; David, Arthur H. G.; Cuerva, Juan M.; Blanco, Victor; Campana, Araceli G.. Category: iodides-buliding-blocks And the article was included in Angewandte Chemie, International Edition in 2020. The article conveys some information:

A cyclophane is reported incorporating two units of a heptagon-containing extended polycyclic aromatic hydrocarbon (PAH) analog of the hexa-peri-hexabenzocoronene (HBC) moiety (hept-HBC). This cyclophane represents a new class of macrocyclic structures that incorporate for the first time seven-membered rings within extended PAH frameworks. The saddle curvature of the hept-HBC macrocycle units induced by the presence of the nonhexagonal ring along with the flexible alkyl linkers generate a cavity with shape complementarity and appropriate size to enable π interactions with fullerenes. Therefore, the cyclophane forms host-guest complexes with C60 and C70 with estimated binding constants of Ka=420±2 M-1 and Ka=(6.49±0.23)x103 M-1, resp. As a result, the macrocycle can selectively bind C70 in the presence of an excess of a mixture of C60 and C70.1-Bromo-4-iodobenzene(cas: 589-87-7Category: iodides-buliding-blocks) 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..Category: iodides-buliding-blocks 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

《Aminoalkyl radicals as halogen-atom transfer agents for activation of alkyl and aryl halides》 was published in Science (Washington, DC, United States) in 2020. These research results belong to Constantin, Timothee; Zanini, Margherita; Regni, Alessio; Sheikh, Nadeem S.; Julia, Fabio; Leonori, Daniele. SDS of cas: 589-87-7 The article mentions the following:

Organic halides are important building blocks in synthesis, but their use in (photo)redox chem. is limited by their low reduction potentials. Halogen-atom transfer remains the most reliable approach to exploit these substrates in radical processes despite its requirement for hazardous reagents and initiators such as tributyltin hydride. In this study, we demonstrate that α-aminoalkyl radicals, easily accessible from simple amines, promote the homolytic activation of carbon-halogen bonds with a reactivity profile mirroring that of classical tin radicals. This strategy conveniently engages alkyl and aryl halides in a wide range of redox transformations to construct sp3-sp3, sp3-sp2, and sp2-sp2 carbon-carbon bonds under mild conditions with high chemoselectivity. 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) 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,dibromostyrenesSDS of cas: 589-87-7

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