Month: October 2022

《Sustainable Ligand-Free Heterogeneous Palladium-Catalyzed Sonogashira Cross-Coupling Reaction in Deep Eutectic Solvents》 was written by Messa, Francesco; Dilauro, Giuseppe; Perna, Filippo M.; Vitale, Paola; Capriati, Vito; Salomone, Antonio. Application of 90-14-2 And the article was included in ChemCatChem in 2020. The article conveys some information:

The com. available and cheap Pd/C was found to promote Sonogashira couplings in the environmentally friendly choline chloride/glycerol eutectic mixture in the absence of external ligands. Under heterogeneous conditions, (hetero)aryl iodides ArI (Ar = naphthalen-1-yl, thiophen-2-yl, 3-chlorophenyl, etc.) were successfully coupled with both aromatic and aliphatic alkynes RCCH (R = trimethylsilyl, pentyl, Ph, etc.) in yields ranging from 50 to 99% within 3 h at 60°C. The aforementioned catalytic system proved to be effective also towards electron-rich iodides, which are notoriously known to be poorly reactive in Pd-catalyzed Sonogashira coupling reactions. The eutectic mixture and the catalyst could easily and successfully be recycled up to four times with an E-factor as low as 24.4. In the part of experimental materials, we found many familiar compounds, such as 1-Iodonaphthalene(cas: 90-14-2Application of 90-14-2)

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.Application of 90-14-2

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

《STM apparent height measurements of molecular wires with different physical length attached on 2-D phase separated templates for evaluation of single molecular conductance》 was written by Iizuka, Tomoya; Shimizu, Daiki; Matsuda, Kenji. Recommanded Product: 1-Bromo-4-iodobenzene And the article was included in RSC Advances in 2020. The article conveys some information:

Single mol. conductance of mol. wires is effectively evaluated by the combination of STM apparent height measurement and a 2-D phase separation technique. Previously the method was only applied to a set of mol. wires with the same phys. length, but herein we applied the method to thienylene-based and phenylene-based mol. wires with different phys. lengths. By considering the difference in phys. mol. height including thermal contribution of conformational isomers, the conductance ratio was determined to be 1.3 ± 0.7, which is in agreement with the reported value determined by a break-junction method. The experimental process involved the reaction of 1-Bromo-4-iodobenzene(cas: 589-87-7Recommanded Product: 1-Bromo-4-iodobenzene)

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..Recommanded Product: 1-Bromo-4-iodobenzene 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

Li, Hongfang; Khan, Ijaz; Li, Meiqi; Wang, Zheng; Wu, Xue; Ding, Kuiling; Zhang, Yong Jian published their research in Organic Letters in 2021. The article was titled 《Pd-Catalyzed Regio- and Enantioselective Aminoarylation of Allenols with Aryl Iodides and 2-Pyridones》.Application of 90-14-2 The article contains the following contents:

A new asym. catalytic protocol for the synthesis of enantioenriched N-allyl 2-pyridones has been developed via the first Pd-catalyzed regio- and enantioselective aminoarylation of allenols with aryl iodides and 2-pyridones. By using a palladium complex generated in situ from Pd2(dba)3·CHCl3 and (S,S,S)-SKP as a catalyst, the three-component aminoarylation proceeded smoothly to afford a variety of functionalized N-allylic 2-pyridones in high yields with good regioselectivities and excellent enantioselectivities. The experimental process involved the reaction of 1-Iodonaphthalene(cas: 90-14-2Application of 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.Application of 90-14-2

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

Cheng, Sidi; Luo, Yu; Yu, Ting; Li, Jing; Gan, Chunfang; Luo, Shuang; Zhu, Qiang published an article in 2022. The article was titled 《Palladium-Catalyzed Four-Component Cascade Imidoyl-Carbamoylation of Unactivated Alkenes》, and you may find the article in ACS Catalysis.HPLC of Formula: 15164-44-0 The information in the text is summarized as follows:

A 1,2-difunctionalization of an unactivated alkene, imidoyl-carbamoylation were developed through a palladium-catalyzed four-component cascade reaction involving aryl iodide, alkenyl isocyanide, CO and amine. Continuous migratory insertion of three different functionalities to the Pd(II) intermediate generated from the previous step took place in a well-defined sequence. Four chem. bonds, including three C-C bonds and one C-N bond, were formed in this cascade process, leading to a convenient and convergent access to acetamides substituted with five- to seven-membered cyclic ketoimines. In addition, an extra C-N bond was formed through in-situ or postreaction cyclization of the amido NH to the ketoimine moiety, providing a facile one-pot access to pyrrolo-fused heterocycles. The experimental part of the paper was very detailed, including the reaction process of 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

Cui, Wenwen; Li, Xufeng; Guo, Guoju; Song, Xiuyan; Lv, Jian; Yang, Daoshan published an article in 2022. The article was titled 《Radial Type Ring Opening of Sulfonium Salts with Dichalcogenides by Visible Light and Copper Catalysis》, and you may find the article in Organic Letters.Computed Properties of C6H4ClI The information in the text is summarized as follows:

Herein, a copper-catalyzed, blue-light-induced free radical type ring opening of sulfonium salts with dichalcogenides has been initially developed. The developed method features an inexpensive copper catalyst and a broad substrate scope, affording practical access to alkyl chalcogenides in high yields. This reaction presents a novel ring-opening model of sulfonium salts, which breaks the limitation that only the nucleophilic ring-opening reaction could form C-heteroatom bonds and C-C bonds. The experimental process involved the reaction of 1-Chloro-3-iodobenzene(cas: 625-99-0Computed Properties of C6H4ClI)

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. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine.Computed Properties of C6H4ClI

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

In 2022,Jiang, Kun; Li, Shi-Jun; Liu, Qing-Peng; Yu, Ning; Li, Yu-Lin; Zhou, Yu-Qiang; He, Kui-Cheng; Lin, Jing; Zheng, Ting-Yu; Lang, Jian; Lan, Yu; Wei, Ye published an article in Chemical Science. The title of the article was 《Iminyl radical-triggered relay annulation for the construction of bridged aza-tetracycles bearing four contiguous stereogenic centers》.Recommanded Product: 4-Iodobenzoic acid The author mentioned the following in the article:

An unprecedented, iminyl radical-triggered relay annulation from oxime-derived peresters and azadienes, which showed good substrate scope and functional group compatibility, and could deliver various bridged I [X = CH2, O; R1 = Ph, 4-methylphenyl, 4-methoxyphenyl, etc.] and II [R2 = Ph, 3-methylphenyl, 4-methoxyphenyl; R3 = propan-2-yl, Bu, hexan-2-yl, etc.] with complex mol. topol. and four contiguous stereogenic centers (dr > 19 : 1) in a single operation. This transformation represented the first example of trifunctionalization of iminyl radicals through simultaneous formation of one C-N and two C-C bonds. DFT calculation studies were conducted to obtain an in-depth insight into the reaction pathways, which revealed that the reactions involved an interesting 1,6-hydrogen atom transfer process. In the experiment, the researchers used 4-Iodobenzoic acid(cas: 619-58-9Recommanded Product: 4-Iodobenzoic acid)

4-Iodobenzoic acid(cas: 619-58-9) 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. Recommanded Product: 4-Iodobenzoic acid 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

In 2022,Gao, Zezhong; Wang, Hang; Zhou, Chunlin; Wang, Ning; Li, Shangda; Li, Gang published an article in Organic Letters. The title of the article was 《Formal C-H/C-I Metathesis: Site-Selective C-H Iodination of 2-Aryl Benzoic Acid Derivatives Using Aryl Iodide》.Name: 2-Iodobenzoic acid The author mentioned the following in the article:

A protocol of remote site-selective C-H iodination of 2-aryl benzoic acid derivatives via formal C(sp2)-H/C(sp2)-I metathesis using readily available 1-iodo-4-methoxy-2-nitrobenzene as the mild iodinating reagent was reported herein. A range of 2-aryl benzoic acid derivatives including 2-(naphthalen-1-yl)benzoic acids and [1,1′-binaphthalene]-2-carboxylic acids were iodinated under mild conditions to give valuable iodinated products in a site- and chemo-selective fashion. The experimental part of the paper was very detailed, including the reaction process of 2-Iodobenzoic acid(cas: 88-67-5Name: 2-Iodobenzoic acid)

2-Iodobenzoic acid(cas: 88-67-5) belongs to organic iodides. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.Name: 2-Iodobenzoic acidIodo 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.

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

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