Category: iodides-buliding-blocks

Meng, Qi; Zhang, Lian; Zhu, Xinhui; Teng, Qiaoqiao published their research in ChemistrySelect in 2021. The article was titled 《Synthesis of 9-O-Arylated Berberine with a Polystyrene Resin Supported Copper(II) Catalyst》.Safety of 4-Iodopyridine The article contains the following contents:

A series of polyfluorobenzene, pyridine and aniline substituted berberine derivatives I (Ar = Ph, 4-H2NC6H4, 3-pyridyl, etc.) were prepared via resin-supported Cu(II) catalyzed cross-coupling reactions of tetrahydroberberrubine with iodoarenes and subsequent I2 oxidation The best catalyst, a polyethyleneimine functionalized polystyrene supported Cu2+ (PSAPA·Cu(II)), could be reused for at least 5 runs without significant loss of catalytic activity. Comparative studies on the morphol. and porous structures of the materials suggested a catalyst with a moderate sp. surface area and larger pore diameters was more active in catalyzing the cross-coupling reactions.4-Iodopyridine(cas: 15854-87-2Safety of 4-Iodopyridine) was used in this study.

4-Iodopyridine(cas: 15854-87-2) belongs to pyridine. In industry and in the lab, pyridine is used as a reaction solvent, particularly when its basicity is useful, and as a starting material for synthesizing some herbicides, fungicides, and antiseptics.Safety of 4-Iodopyridine

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

《Concise synthesis of a tetrasaccharide related to the repeating unit of the cell wall O-antigen of Salmonella enterica O60》 was written by Gucchait, Arin; Shit, Pradip; Misra, Anup Kumar. Recommanded Product: 1-Iodopyrrolidine-2,5-dione And the article was included in Tetrahedron in 2020. The article conveys some information:

Synthesis of a tetrasaccharide related to the repeating unit of the cell wall O-antigen of Salmonella enterica O60 has been achieved by sequential glycosylations in very good yield. Use of p-methoxybenzyl group (PMB) as an in situ removable protecting group allowed obtaining the desired compound in less number of steps. Synthesis of a beta-D-mannosidic linkage present in the mol. has been successfully achieved using D-mannosyl thioglycoside donor having a p-methoxybenzyl (PMB) group at remote C-3 position. A combination of N-iodosuccinimide (NIS) and perchloric acid supported over silica (HClO4-SiO2) has been used as thiophilic glycosylation promoter in glycosylation reactions. Thioglycoside of 3-amino-3-deoxy-D-fucose has been prepared and used in the synthetic scheme for its incorporation in α-glycosidic linkage. In the experiment, the researchers used 1-Iodopyrrolidine-2,5-dione(cas: 516-12-1Recommanded Product: 1-Iodopyrrolidine-2,5-dione)

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. Recommanded Product: 1-Iodopyrrolidine-2,5-dione

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

《A new approach to large scale production of dimethyl sulfone: a promising and strong recyclable solvent for ligand-free Cu-catalyzed C-C cross-coupling reactions》 was published in Green Chemistry in 2020. These research results belong to Cheng, Shen; Wei, Wei; Zhang, Xingyu; Yu, Hewei; Huang, Mingming; Kazemnejadi, Milad. Name: 1-Iodonaphthalene The article mentions the following:

Di-Me sulfone (DMSN) was easily prepared through efficient oxidation of DMSO (DMSO) and used as a strong and green solvent for organic reactions. A mixture of HNO3/NaOCl was used as an oxidizing agent for efficient oxidation of DMSO to DMSN. The effect of DMSN was evaluated for copper-catalyzed coupling reactions. It is worth noting that DMSN could play the role of a ligand for copper ions. A general survey was accomplished for various types of C-C cross-coupling reactions catalyzed by CuI in DMSN in the absence of any ligand. Moderate to good yields were achieved for Sonogashira, Heck, and Suzuki cross-coupling reactions. Finally, DMSN was recovered and reused for several consecutive runs without any loss of its activity. The experimental process involved the reaction of 1-Iodonaphthalene(cas: 90-14-2Name: 1-Iodonaphthalene)

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

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

《Metal-Free Chemoselective Reaction of Sulfoxonium Ylides and Thiosulfonates: Diverse Synthesis of 1,4-Diketones, Aryl Sulfursulfoxonium Ylides, and β-Keto Thiosulfones Derivatives》 was published in Organic Letters in 2020. These research results belong to Wang, Fei; Liu, Bo-Xi; Rao, Weidong; Wang, Shun-Yi. Computed Properties of C3H9IOS The article mentions the following:

A diverse chemoselective insertion reaction of sulfoxonium ylides and thiosulfonates under transition-metal-free conditions is developed, which successfully affords 1,4-diketone compounds, arylthiosulfoxide-ylides, and β-keto thiosulfones, resp. The nucleophilic addition of two mol. sulfoxonium ylides to construct sulfone-substituted 1,4-dione compounds is the highlight of this work. In the experiment, the researchers used many compounds, for example, Trimethylsulfoxonium iodide(cas: 1774-47-6Computed Properties 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.Computed Properties of C3H9IOS

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

《Mechanistic Insights for Aniline-Catalyzed Halogenation Reactions》 was published in ChemCatChem in 2020. These research results belong to Qu, Zheng-Wang; Zhu, Hui; Grimme, Stefan. Related Products of 516-12-1 The article mentions the following:

Lewis base catalyzed electrophilic aromatic halogenation using N-halosuccinimides (NsX; X=Cl, Br, I) under mild conditions has attracted much attention, but the detailed mechanism remains elusive. Using the aniline MesNH2 and anisole PhOMe as the typical base catalyst and aromatic substrate, resp., a novel mechanism is revealed by extensive DFT calculations The autogenic protonation of imine XMes=NH (via Mes=NH+ mediated dimerization of MesNH2) is crucial to initialize the electrophilic halonium X+ transfer to nucleophilic substrates. It is shown that the aniline MesNH2 and more basic imine XMes=NH may act as efficient halonium X+ and proton H+ shuttles, resp., connected by the arenium XMesNH2+. Non-coordinating MesNH3+ salts are suggested as efficient catalyst for electrophilic iodination. Without suitable stabilization of the highly basic anion Ns-, the generally accepted concept of Lewis base catalyst as simple X+ shuttle will never work efficiently due to a high thermodn. barrier. In general, autogenic or addnl. acid additives should be used for more efficient Lewis base catalyzed halogenation. In the experiment, the researchers used many compounds, for example, 1-Iodopyrrolidine-2,5-dione(cas: 516-12-1Related Products 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. Related Products of 516-12-1

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

The author of 《Palladium-Catalyzed β-C-H Arylation of Aliphatic Aldehydes and Ketones Using Amino Amide as a Transient Directing Group》 were Dong, Cong; Wu, Liangfei; Yao, Jianwei; Wei, Kun. And the article was published in Organic Letters in 2019. Reference of 1-Iodo-4-methylbenzene The author mentioned the following in the article:

This paper describes a new amino-amide-based transient directing group (TDG). The TDG can exhibit better performance in the Pd-catalyzed arylation of aliphatic aldehydes and ketones. This reaction showed good substrate compatibility and regioselectivity. The results indicated that 3-amino-N-isopropylpropionamide was more beneficial to the β-arylation of aliphatic aldehydes than other TDGs under relatively mild conditions.1-Iodo-4-methylbenzene(cas: 624-31-7Reference of 1-Iodo-4-methylbenzene) was used in this study.

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.Reference of 1-Iodo-4-methylbenzene

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

Synthetic Route of C6H5IOIn 2021 ,《Access to S-Stereogenic Free Sulfoximines via Bifunctional Phosphonium Salt-Catalyzed Desymmetrization of Bisphenols》 was published in ACS Catalysis. The article was written by Fang, Siqiang; Liu, Zanjiao; Zhang, Hongkui; Pan, Jianke; Chen, Yuan; Ren, Xiaoyu; Wang, Tianli. The article contains the following contents:

Sulfur-stereogenic sulfoximines particularly with a free N-H unit exhibit intriguing chem. and biol. activities, and thus have received continuous attention from chemists. However, there are currently no examples of guiding catalytic asym. strategies available to directly access these mols. Herein, an efficient and practical protocol for the direct enantioenrichment of free N-H sulfoximines via a bifunctional phosphonium salt-catalyzed desymmetrization triggered by the Atherton-Todd reaction together with a further extended nucleophilic acyl substitution-type reaction has been disclosed. A series of free N-H sulfoximines bearing an assortment of aromatic groups (70 examples) was tolerated in this desymmetrization with incidentally involving minority kinetic resolution (KR). The desymmetrized products can be easily transformed into chiral sulfoxides and other classes of active sulfur-stereogenic compounds Mechanistic studies provided insights into the reaction pathway particularly suggesting a desymmetrization/KR synergic process, and also offered support on hydrogen-bonding interactions as the key elements to successful stereocontrol. In the experiment, the researchers used 3-Iodophenol(cas: 626-02-8Synthetic Route of C6H5IO)

3-Iodophenol(cas: 626-02-8) 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.Synthetic Route of C6H5IO

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

Computed Properties of C6H5ClINIn 2022 ,《Spirocyclizative remote arylcarboxylation of nonactivated arenes with CO2 via visible-light-induced reductive dearomatization》 was published in CCS Chemistry. The article was written by Gao, Yuzhen; Wang, Hao; Chi, Zhuomin; Yang, Lei; Zhou, Chunlin; Li, Gang. The article contains the following contents:

Herein, a novel strategy to achieve a visible-light-induced spirocyclizative remote arylcarboxylation of nonactivated arenes including naphthalenyl- and phenyl-bearing aromatics with CO2 under mild conditions through a radical-polar crossover cascade (RPCC) was described. This reductive dearomatization protocol rapidly delivered a broad range of spirocyclic and valuable carboxylic acid derivatives e.g., I from readily accessible aromatic precursors with generally good regioselectivity and chemoselectivity. In the experimental materials used by the author, we found 4-Chloro-2-iodoaniline(cas: 63069-48-7Computed Properties of C6H5ClIN)

4-Chloro-2-iodoaniline(cas: 63069-48-7) belongs to anime. To avoid the problem of multiple alkylation, methods have been devised for “blocking” substitution so that only one alkyl group is introduced. The Gabriel synthesis is one such method; it utilizes phthalimide, C6H4(CO)2NH, whose one acidic hydrogen atom has been removed upon the addition of a base such as KOH to form a salt.Computed Properties of C6H5ClIN

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

Product Details of 625-99-0In 2019 ,《C(sp3)-H Bond Arylation and Amidation of Si-Bound Methyl Group via Directing Group Strategy》 was published in ACS Catalysis. The article was written by Han, Jie-Lian; Qin, Ying; Zhao, Dongbing. The article contains the following contents:

Silylmethyl functionalization provides a general and efficient access to diverse organosilanes. The traditional methods for silylmethyl functionalization often involved silylmethylmetals or silylmethyl halides. In recent years, a C-H activation strategy has become one of the most attractive alternatives in organic synthesis. Authors envisioned that the attachment of a coordinating group at silicon of methylsilanes provides the opportunity to modify the silylmethyl group via directed C-H bond functionalization. However, despite employment of silicon tethers bearing a directing group (DG) for C(sp2)-H functionalization has been well established due to the fact that the silicon tethers are easily installable and removable/modifiable, applying this concept toward C(sp3)-H functionalization remains underdeveloped. Herein, authors successfully developed IrIII/RhIII-catalyzed C-H bond arylation/amidation of silyl Me group by using directing group strategy, which constitutes the most powerful access to benzylsilanes and amino-substituted silanes. Moreover, they demonstrated that the pyridine directing group on silicon atom can be easily removed, and the starting materials can also be efficiently recovered, which are different from those of pyridine-directed C-H functionalization of C-bound Me group. In the experiment, the researchers used many compounds, for example, 1-Chloro-3-iodobenzene(cas: 625-99-0Product Details of 625-99-0)

1-Chloro-3-iodobenzene(cas: 625-99-0) 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.Product Details of 625-99-0

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

Electric Literature of C10H18INO2In 2022 ,《Metal-free visible-light-initiated direct C3 alkylation of quinoxalin-2(1H)-ones and coumarins with unactivated alkyl iodides》 appeared in Green Chemistry. The author of the article were Sun, Jun; Yang, Hua; Zhang, Bo. The article conveys some information:

For the first time, a visible-light-promoted direct C3 alkylation of quinoxalin-2(1H)-ones and coumarins using readily accessible unactivated alkyl iodides as alkylation reagents was reported. By applying this new approach, a broad range of valuable 3-alkylated quinoxalin-2(1H)-ones and coumarins (55 examples) were facilely obtained at room temperature, thus showing the wide utility of this protocol. Notably, this practical reaction occurred under metal- and external photocatalyst-free conditions and exhibited a broad substrate scope and high functional-group tolerance. The experimental process involved the reaction of tert-Butyl 4-iodopiperidine-1-carboxylate(cas: 301673-14-3Electric Literature of C10H18INO2)

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.Electric Literature of C10H18INO2

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