Author: Jessica.F

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

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

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

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

《Revisiting the Urech Synthesis of Hydantoins: Direct Access to Enantiopure 1,5-Substituted Hydantoins Using Cyanobenziodoxolone》 was written by Declas, Nina; Le Vaillant, Franck; Waser, Jerome. Category: iodides-buliding-blocksThis research focused onurech synthesis enantiopure substituted hydantoin preparation; hydantoin preparation hypervalent iodine cyanation reagent amino acid reaction. The article conveys some information:

A method for the synthesis of enantiopure 1,5-substituted hydantoins was developed using a hypervalent iodine cyanation reagent (cyanobenziodoxolone, CBX) as a source of electrophilic carbon. Starting from inexpensive com. available enantiopure protected amino acids, the method allowed the synthesis of various hydantoins without epimerization. Formation of hydantoins from dipeptides was also possible, but partial epimerization was observed in this case. This synthetic strategy is user friendly as CBX is a bench-stable easy-to-handle crystalline reagent and avoids conventional multistep protocols, thus allowing the facile synthesis of a library of chiral hydantoins. In addition to this study using 2-Iodobenzoic acid, there are many other studies that have used 2-Iodobenzoic acid(cas: 88-67-5Category: iodides-buliding-blocks) was used in this study.

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. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine.Category: iodides-buliding-blocks

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

Quality Control of (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthaleneOn September 17, 2021 ,《Catalytic Asymmetric (3 + 3) Cycloaddition of Oxyallyl Zwitterions with α-Diazomethylphosphonates》 was published in Organic Letters. The article was written by Liu, Yan; Peng, Xian; She, Rui; Zhou, Xin; Peng, Yungui. The article contains the following contents:

The unique structure of oxyallyls represents a significant challenge for their catalytic asym. applications. Herein, an unprecedented chiral imidodiphosphoric acid-catalytic enantioselective (3 + 3) cycloaddition between oxyallyl zwitterions generated in situ from α-haloketones and α-diazomethylphosphonates was developed. Pharmaceutically interesting chiral pyridazine-4(1H)-ones were obtained in up to 98% yields with excellent stereoselectivities (up to 99% ee, > 99:1 dr). In the experiment, the researchers used (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene(cas: 189518-78-3Quality Control of (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene)

(R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene(cas: 189518-78-3) 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. Organic iodides can be alkyl, alkenyl, or alkynyl, and all of them are very reactive toward with many kinds of nucleophiles.Quality Control of (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene

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

Application In Synthesis of 2-Chloro-5-iodo-3-(trifluoromethyl)pyridineOn September 2, 2022 ,《PdII-Catalyzed γ-C(sp3)-H (Hetero)arylation of Ketones Enabled by Transient Directing Groups》 was published in ACS Catalysis. The article was written by Li, Yi-Hao; Ouyang, Yuxin; Chekshin, Nikita; Yu, Jin-Quan. The article contains the following contents:

Pd(II)-catalyzed γ-C(sp3)-H (hetero)arylation of aliphatic ketones is developed using α-amino acids as transient directing groups (TDG). A variety of aliphatic ketones were (hetero)arylated at the γ-position via a 5,6-membered fused cyclopalladation intermediate to afford the remotely arylated products in up to 88% yield. The crucial ligand effect of 2-pyridone is further enhanced by reducing the loading of acid additives. Consequentially, the improved reactivity of this catalytic system has also made possible the cyclic γ-methylene C(sp3)-H arylation of ketones. Mechanistic investigation and comparison to the γ-C-H arylation of aldehydes revealed a structural insight for designing site-selective TDG. The results came from multiple reactions, including the reaction of 2-Chloro-5-iodo-3-(trifluoromethyl)pyridine(cas: 887707-25-7Application In Synthesis of 2-Chloro-5-iodo-3-(trifluoromethyl)pyridine)

2-Chloro-5-iodo-3-(trifluoromethyl)pyridine(cas: 887707-25-7) belongs to pyridine. Pyridine, its benzo and pyridine-based compounds play diverse roles in organic chemistry. As ligands, solvents, and catalysts they facilitate reactions; thus descriptions of these new ligands and their applications abound each year.Application In Synthesis of 2-Chloro-5-iodo-3-(trifluoromethyl)pyridine

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

In 2015,Miao, Jinmin; Yang, Ke; Kurek, Martin; Ge, Haibo published 《Palladium-Catalyzed Site-Selective Fluorination of Unactivated C(sp3)-H Bonds》.Organic Letters published the findings.Product Details of 624-73-7 The information in the text is summarized as follows:

The transition-metal-catalyzed direct C-H bond fluorination is an attractive synthetic tool toward the preparation of organofluorines. While many methods exist for the direct sp3 C-H functionalization, site-selective fluorination of unactivated sp3 carbons remains a challenge. Direct, highly site-selective and diastereoselective fluorination of aliphatic amides via a palladium-catalyzed bidentate ligand-directed C-H bond functionalization process on unactivated sp3 carbons is reported. With this approach, a wide variety of β-fluorinated amino acid derivatives and aliphatic amides, important motifs in medicinal and agricultural chem., were prepared with palladium acetate as the catalyst and Selectfluor as the fluorine source. The experimental part of the paper was very detailed, including the reaction process of 1,2-Diiodoethane(cas: 624-73-7Product Details of 624-73-7)

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.Product Details of 624-73-7

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

In 2019,Tetrahedron Letters included an article by Fu, Fang; Gurung, Laxman; Czaun, Miklos; Mathew, Thomas; Prakash, G. K. Surya. Synthetic Route of C6H4BrI. The article was titled 《ipso-Bromination/iodination of arylboronic acids: Poly(4-vinylpyridine)-Br2/I2 complexes as safe and efficient reagents》. The information in the text is summarized as follows:

Poly(4-vinyl pyridine) supported bromine/iodine complexes were prepared and probed for ipso-bromination/iodination of arylboronic acids ArB(OH)2 (Ar = 4-methylphenyl, 3-nitrophenyl, naphthalen-2-yl, etc.). These solid complexes with catalytic amount of additive are found to be safe and efficient reagent system for the ipso-bromination/iodination. The reaction occurs under mild conditions and tolerates various functional groups resulting in products ArX (X = Br, I) with high selectivity and yields. The results came from multiple reactions, including the reaction of 1-Bromo-4-iodobenzene(cas: 589-87-7Synthetic Route of C6H4BrI)

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,dibromostyrenesSynthetic Route of C6H4BrI

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

In 2019,Green Chemistry included an article by Gong, Xinchi; Wu, Jie; Meng, Yunge; Zhang, Yulan; Ye, Long-Wu; Zhu, Chunyin. Product Details of 624-31-7. The article was titled 《Ligand-free palladium catalyzed Ullmann biaryl synthesis: ‘household’ reagents and mild reaction conditions》. The information in the text is summarized as follows:

A palladium catalyzed Ullmann biaryl ArAr1, Ar1Ar1, ArAr, (Ar = 4-CNC6H4, pyridin-2-yl, 3-MeC6H4, etc.; Ar1 = 4-CNC6H4, 4-MeOC6H4) synthesis has been developed using hydrazine hydrate as the reducing reagent at room temperature The combination of Pd(OAc)2 and hydrazine hydrate works smoothly for the coupling of both electron-rich and electron-deficient aryl iodides ArI and Ar1I, as well as 2-iodopyridine, leading to a wide range of biaryls in good to excellent yields. The reaction requires only 1 mol% Pd(OAc)2 and the in situ generated palladium nanoparticles are found to be active catalysts. After reading the article, we found that the author used 1-Iodo-4-methylbenzene(cas: 624-31-7Product Details of 624-31-7)

1-Iodo-4-methylbenzene(cas: 624-31-7) undergoes Suzuki-Miyaura coupling reaction with phenylboronic acid catalyzed by (Ni,Mg)3Si2O5(OH)4 solid-solution nanotubes loaded with palladium.Product Details of 624-31-7

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