Month: October 2022

Mcnamee, Ryan E.; Haugland, Marius M.; Nugent, Jeremy; Chan, Rachel; Christensen, Kirsten E.; Anderson, Edward A. published their research in Chemical Science in 2021. The article was titled 《Synthesis of 1,3-disubstituted bicyclo[1.1.0]butanes via directed bridgehead functionalization》.Application In Synthesis of 3-Iodophenol The article contains the following contents:

Bicyclo[1.1.0]butanes (BCBs) are increasingly valued as intermediates in ‘strain release’ chem. for the synthesis of substituted four membered rings and bicyclo[1.1.1]pentanes, with applications including bioconjugation processes. Variation of the BCB bridgehead substituents can be challenging due to the inherent strain of the bicyclic scaffold, often necessitating linear syntheses of specific BCB targets. Here authors report the first palladium catalyzed cross-coupling on pre-formed BCBs which enables a ‘late stage’ diversification of the bridgehead position, and the conversion of the resultant products into a range of useful small ring building blocks. In addition to this study using 3-Iodophenol, there are many other studies that have used 3-Iodophenol(cas: 626-02-8Application In Synthesis of 3-Iodophenol) was used in this study.

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. Application In Synthesis of 3-Iodophenol 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

Ji, Liangshuo; Qiao, Jiamin; Liu, Junjie; Tian, Miaomiao; Lu, Kui; Zhao, Xia published their research in Tetrahedron Letters in 2021. The article was titled 《Metal-free chalcogenation of cycloketone oxime esters with dichalcogenides》.Name: 1-Bromo-3-iodobenzene The article contains the following contents:

The metal-free chalcogenation of cycloketone oxime esters with dichalcogenides via a radical process was reported. Because of the metal-free condition and use of readily accessible dichalcogenides, this method was an effective and green strategy for the synthesis of chalcogen-substituted butyronitrile. In the experimental materials used by the author, we found 1-Bromo-3-iodobenzene(cas: 591-18-4Name: 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.Name: 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

Liu, Xian-Guan; Dong, Ci-Shuang; Li, Fei; Zhang, Bo published an article in 2021. The article was titled 《Manganese-Mediated Direct Functionalization of Hantzsch Esters with Alkyl Iodides via an Aromatization-Dearomatization Strategy》, and you may find the article in Organic Letters.Computed Properties of C10H18INO2 The information in the text is summarized as follows:

Manganese-mediated direct functionalization of the Hantzsch esters with readily accessible alkyl iodides through an aromatization-dearomatization strategy was reported for the first time. Applying this protocol, a library of valuable 4-alkyl-1,4-dihydropyridines were facilely afforded in good yields. This simple and practical reaction proceeded under visible-light irradiation at room temperature and displays high functional-group compatibility. Addnl., the method was applicable for gram-scale synthesis and late-stage functionalization of complex mols. The experimental process involved the reaction of tert-Butyl 4-iodopiperidine-1-carboxylate(cas: 301673-14-3Computed Properties of C10H18INO2)

tert-Butyl 4-iodopiperidine-1-carboxylate(cas: 301673-14-3) 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.Computed Properties of C10H18INO2

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

Wang, Dong-Chao; Cheng, Peng-Peng; Yang, Ting-Ting; Wu, Pan-Pan; Qu, Gui-Rong; Guo, Hai-Ming published an article in 2021. The article was titled 《Asymmetric Domino Heck/Dearomatization Reaction of β-Naphthols to Construct Indole-Terpenoid Frameworks》, and you may find the article in Organic Letters.Category: iodides-buliding-blocks The information in the text is summarized as follows:

A palladium-catalyzed enantioselective Heck cyclization/dearomatization cascade via capturing the cyclized Heck π-allylpalladium intermediate by β-naphthols is reported, which provides a new strategy for the construction of chiral indole-terpenoid frameworks. This method affords indole-functionalized β-naphthalenone compounds bearing an all-carbon-substituted quaternary chiral center in excellent yields (up to 92%) and enantioselectivities (up to 94% ee). In addition, the utility of this method is showcased by the gram-scale syntheses and diverse transformations of the dearomatized products. In addition to this study using 4-Chloro-2-iodoaniline, there are many other studies that have used 4-Chloro-2-iodoaniline(cas: 63069-48-7Category: iodides-buliding-blocks) was used in this study.

4-Chloro-2-iodoaniline(cas: 63069-48-7) belongs to anime. Amine, any member of a family of nitrogen-containing organic compounds that is derived, either in principle or in practice, from ammonia (NH3). Naturally occurring amines include the alkaloids, which are present in certain plants; the catecholamine neurotransmitters (i.e., dopamine, epinephrine, and norepinephrine); and a local chemical mediator, histamine, that occurs in most animal tissues.Category: iodides-buliding-blocks

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

Cheng, Yaohang; Yu, Shijie; He, Yuhang; An, Guanghui; Li, Guangming; Yang, Zhenyu published an article in 2021. The article was titled 《C4-arylation and domino C4-arylation/3,2-carbonyl migration of indoles by tuning Pd catalytic modes: Pd(I)-Pd(II) catalysis vs. Pd(II) catalysis》, and you may find the article in Chemical Science.Application In Synthesis of 4-Iodobenzaldehyde The information in the text is summarized as follows:

Efficient C4-arylation and domino C4-arylation/3,2-carbonyl migration of indoles was developed. The former route enables C4-arylation in a highly efficient and mild manner and the latter route provides an alternative straightforward protocol for synthesis of C2/C4 disubstituted indoles. The mechanism studies imply that the different reaction pathways were tuned by the distinct acid additives, which led to either the Pd(I)-Pd(II) pathway or Pd(II) catalysis. In the experiment, the researchers used many compounds, for example, 4-Iodobenzaldehyde(cas: 15164-44-0Application In Synthesis of 4-Iodobenzaldehyde)

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.Application In Synthesis of 4-Iodobenzaldehyde

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

Pei, Xiaoyan; Xiang, Deng; Luo, Zhengxiu; Lei, Fukun; Guo, Zhanglong; Liu, Dong; Zhao, Zhigang; Ran, Maofei; Dai, Tao published an article in 2021. The article was titled 《Catalytic performance of palladium nanoparticles encapsulated within nitrogen-doped carbon during Heck reaction》, and you may find the article in Journal of Catalysis.Application In Synthesis of 1-Bromo-4-iodobenzene The information in the text is summarized as follows:

The Confinement effect is an effective strategy for enhancing the performance of catalysts during various reactions. We developed a strategy to encapsulating Palladium nanoparticles with a dopamine-derived N-doped multilayer carbon shell to catalyze the Heck reaction between iodobenzene and carbon-carbon double-bond compounds (styrene and Me acrylate). The catalytic performances of Pd nanoparticles encapsulated within a N-doped carbon layer (Pd@N-C) and those attached to the external surface of such a layer (Pd/N-C) were evaluated and compared. Pd@N-C exhibited a lower reaction activation energy (78 kJ/mol) than that of Pd/N-C (106 kJ/mol). Thus, the activity of Pd@N-C during the Heck reaction between iodobenzene and Me acrylate was approx. 20 times higher than that of Pd/N-C-200. The results of thermal filtration and recycling tests indicated that Pd@N-C showed a lower degree of leaching than that of Pd/N-C-200 owing to the spatial restriction effect of the cavity in the case of the former. Hence, the superior catalytic performance of Pd@N-C can be ascribed to the confinement of the Pd nanoparticles within the N-doped carbon layer. Finally, we useCinnamatesd these catalysts to synthesize a range of para-substituted iodobenzene derivatives, thus demonstrating the potential of Pd-encapsulating catalysts for use in the Heck reaction on the tech. scale. The experimental part of the paper was very detailed, including the reaction process of 1-Bromo-4-iodobenzene(cas: 589-87-7Application In Synthesis of 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..Application In Synthesis of 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

Zhang, Mingjun; Yu, Mo; Wang, Ziwen; Liu, Yuxiu; Wang, Qingmin published an article in 2022. The article was titled 《Rapid Access to Aliphatic Sulfonamides》, and you may find the article in Organic Letters.Formula: C10H18INO2 The information in the text is summarized as follows:

Herein, a mild, rapid, straightforward method for visible-light-mediated sulfonamide ethylation to afford a diverse array of compounds with C(sp3)-sulfonamide skeletons RS(O)2N(R1)R2 (R = 4-phenylbutyl, 3,3-dimethylbutyl, 2-cyclobutylethyl, 4-(pyridin-2-yl)butyl, etc.; R1 = H, Ph, 2-oxooxolan-3-yl, benzyl, etc.; R2 = H, Me, phenyl) was reported. The method relies on inexpensive, abundant, com. available primary, secondary, and tertiary alkyl carboxylic acids I (R3 = 2-phenylethyl, 2,2-diphenylethyl, 2-(pyridin-3-yl)ethyl, pentyl, etc.) and alkyl iodides R4I (R4 = 2-cyclohexylethyl, pentyl, 4-(trimethylsilyl)butyl, hept-6-yn-1-yl, etc.) as substrates. The method has a broad substrate scope and potential utility for late-stage functionalization of natural products and synthetic medicines and can be expected to facilitate rapid structural diversification of bioactive mols. In addition to this study using tert-Butyl 4-iodopiperidine-1-carboxylate, there are many other studies that have used tert-Butyl 4-iodopiperidine-1-carboxylate(cas: 301673-14-3Formula: C10H18INO2) was used in this study.

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.Formula: C10H18INO2

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

In 2022,Ren, Xiaoxiao; Gao, Xing; Min, Qiao-Qiao; Zhang, Shu; Zhang, Xingang published an article in Chemical Science. The title of the article was 《(Fluoro)alkylation of alkenes promoted by photolysis of alkylzirconocenes》.SDS of cas: 301673-14-3 The author mentioned the following in the article:

An unprecedented example of alkylzirconocenes Cp2ZrCl(CH2)2R (R = Bn, dimethyl(phenyl)silyl, trimethylsilyl, etc.) promoted difluoroalkylation of alkyl- and silyl-alkenes RCH=CH2 with a variety of unactivated difluoroalkyl iodides and bromides R1C(F2)X (R1 = [(ethanesulfonyl)oxy]methyl, (morpholin-4-yl)carbonyl, 3-[(4-chlorophenyl)carbonyloxy]propyl, etc.; X = I, Br) under the irradiation of visible light without a catalyst. The resulting difluoroalkylated compounds RC(F2)R1 can serve as versatile synthons in organic synthesis. The reaction can also be applied to activated difluoroalkyl, trifluoromethyl, perfluoroalkyl, monofluoroalkyl, and nonfluorinated alkyl halides, providing a general method to controllably access fluorinated compounds Preliminary mechanistic studies reveal that a single electron transfer (SET) pathway induced by a Zr(III) species is involved in the reaction, in which the Zr(III) species is generated by the photolysis of alkylzirconocene with blue light. In the experiment, the researchers used tert-Butyl 4-iodopiperidine-1-carboxylate(cas: 301673-14-3SDS of cas: 301673-14-3)

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

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

In 2022,Xu, Chen; Yin, Chenjia; Wu, Wenjun; Ma, Xiang published an article in Science China: Chemistry. The title of the article was 《Tunable room-temperature phosphorescence and circularly polarized luminescence encoding helical supramolecular polymer》.Reference of 1-Bromo-4-iodobenzene The author mentioned the following in the article:

Supramol. polymers with different functionalities have been continuously developed in the past decade because of their indispensable role in soft materials. However, pure organic supramol. polymers with stable room temperature phosphorescence (RTP) emission were very rarely reported for the difficulties of synthesis and achieving RTP in solution Herein, soluble helical supramol. polymers with circularly polarized room-temperature phosphorescence were developed via a facile host-guest strategy. Through assembly, a transition from pure fluorescence to almost pure RTP emission was achieved. Adjusting the asymmetry of guest could easily control the chiroptical property of supramol. polymers. This work provides new opportunities for the design and development of intelligent soft functional soft materials. [graphic not available: see fulltext] In addition to this study using 1-Bromo-4-iodobenzene, there are many other studies that have used 1-Bromo-4-iodobenzene(cas: 589-87-7Reference of 1-Bromo-4-iodobenzene) 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..Reference of 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

In 2022,Ren, Jing; Jia, Meng-Cheng; Du, Feng-Huan; Zhang, Chi published an article in Chinese Chemical Letters. The title of the article was 《A general method for one-step synthesis of monofluoroiodane(III) reagents using silver difluoride》.Safety of 2-Iodobenzoic acid The author mentioned the following in the article:

A new general method for one-step synthesis of four kinds of fluoroiodane(III) reagents by treating the corresponding aryl iodides with silver difluoride (AgF2) was reported. This is the first method applicable for the synthesis of all four fluoroiodane(III) reagents including p-iodotoluene difluoride, fluoro-benziodoxoles, fluoro-benziodoxolones and fluoro-N-acetylbenziodazole. AgF2 was firstly employed in the direct oxidative fluorination of iodobenzene and thus has shown its outstanding oxidation and fluorine-transfer ability. The use of AgF2 has improved the synthesis of fluoroiodane(III) reagents by shortening the reaction steps, avoiding the use of hazardous reagents and simplifying the exptl. operations. It was worth noting that the developed first one-step direct synthetic method for fluoro-benziodoxolones, while fluoro-benziodoxolones can only be synthesized through Cl→F ligand exchange reaction previously. In the experimental materials used by the author, we found 2-Iodobenzoic acid(cas: 88-67-5Safety of 2-Iodobenzoic acid)

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. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.Safety of 2-Iodobenzoic acid

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