Month: October 2022

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

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

Category: iodides-buliding-blocksIn 2021 ,《Room-temperature phosphorescence of a water-soluble supramolecular organic framework》 was published in Chemical Communications (Cambridge, United Kingdom). The article was written by Xu, Chen; Lin, Xiaohan; Wu, Wenjun; Ma, Xiang. The article contains the following contents:

A flexible porous water-soluble supramol. organic framework was developed, which could efficiently exhibit phosphorescence both in an aqueous phase and in a film state at room-temperature In the experiment, the researchers used 1-Bromo-4-iodobenzene(cas: 589-87-7Category: iodides-buliding-blocks)

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

《A New Structural Motif for an Enantiomerically Pure Metallosupramolecular Pd4L8 Aggregate by Anion Templating》 was published in Angewandte Chemie, International Edition in 2014. These research results belong to Klein, Christoph; Guetz, Christoph; Bogner, Maximilian; Topic, Filip; Rissanen, Kari; Luetzen, Arne. Recommanded Product: 189518-78-3 The article mentions the following:

An enantiomerically pure BINOL-based bis(3-pyridyl) ligand 1 assembles into a homochiral [Pd4(1)8] complex upon coordination to tetravalent PdII ions. The formation of this aggregate is templated by two tetrafluoroborate counterions that are encapsulated in two peripheral cavities. The resulting structure is a new structural motif for this kind of metallosupramol. assemblies that arranges the palladium ions in a distorted tetrahedral fashion and forces ligand 1 to adopt two different conformations. Both phenomena are unique and cause an overall three-dimensional structure that has another confined, chiral, and hydrophilic central cavity. The experimental process involved the reaction of (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene(cas: 189518-78-3Recommanded Product: 189518-78-3)

(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. Recommanded Product: 189518-78-3 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

《Enantiomerically Pure Trinuclear Helicates via Diastereoselective Self-Assembly and Characterization of Their Redox Chemistry》 was written by Guetz, Christoph; Hovorka, Rainer; Struch, Niklas; Bunzen, Jens; Meyer-Eppler, Georg; Qu, Zheng-Wang; Grimme, Stefan; Topic, Filip; Rissanen, Kari; Cetina, Mario; Engeser, Marianne; Luetzen, Arne. Computed Properties of C24H20I2O4 And the article was included in Journal of the American Chemical Society on August 20 ,2014. The article conveys some information:

A tris(bipyridine) ligand 1 with two BINOL (BINOL = 2,2′-dihydroxy-1,1′-binaphthyl) groups has been prepared in two enantiomerically pure forms. This ligand undergoes completely diastereoselective self-assembly into D2-sym. double-stranded trinuclear helicates upon coordination to copper(I) and silver(I) ions and to D3-sym. triple-stranded trinuclear helicates upon coordination to copper(II), zinc(II), and iron(II) ions as demonstrated by mass spectrometry, NMR and CD spectroscopy in combination with quantum chem. calculations and x-ray diffraction anal. According to the calculations, the single diastereomers that are formed during the self-assembly process are strongly preferred compared to the next stable diastereomers. Due to this strong preference, the self-assembly of the helicates from racemic 1 proceeds in a completely narcissistic self-sorting manner with an extraordinary high degree of self-sorting that proves the power and reliability of this approach to achieve high-fidelity diastereoselective self-assembly via chiral self-sorting to get access to stereochem. well-defined nanoscaled objects. Furthermore, mass spectrometric methods including electron capture dissociation MSn experiments could be used to elucidate the redox behavior of the copper helicates. After reading the article, we found that the author used (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene(cas: 189518-78-3Computed Properties of C24H20I2O4)

(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. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.Computed Properties of C24H20I2O4

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

《Gold (I/III)-Catalyzed Trifluoromethylthiolation and Trifluoromethylselenolation of Organohalides》 was written by Mudshinge, Sagar R.; Yang, Yuhao; Xu, Bo; Hammond, Gerald B.; Lu, Zhichao. Product Details of 626-02-8This research focused ontrifluoromethyl thioether preparation; silver trifluoromethanethiolate organohalide trifluoromethylthiolation gold redox catalyst; selenoether trifluoromethyl preparation; tetramethylammonium trifluoromethylselenate organohalide trifluoromethylselenolation gold redox catalyst; Cross-Coupling; Gold Catalysis; Organohalides; Trifluoromethylselenolation; Trifluoromethylthiolation. The article conveys some information:

The first C-SCF3/SeCF3 cross-coupling reactions using gold redox catalysis [(MeDalphos)AuCl], AgSCF3 or Me4NSeCF3, and organohalides ArI (Ar = Ph, 4-bromophenyl, 2,6-dimethoxypyridin-3-yl, ec.), (E/Z)-RCH=CHI (R = C(O)OMe, Ph, naphthalen-1-yl, etc.) and R1CCBr (R1 = Ph, 4-fluorophenyl, 4-nitrophenyl, etc.) as substrates are reported. The new methodol. enables a one-stop shop synthesis of aryl/alkenyl/alkynyl trifluoromethylthio- and selenoethers ArSCF3, (E/Z)-RCH=CHSCF3, R1CCSCF3, and RSeCF3 with a broad substrate scope (>60 examples with up to 97% isolated yield). The method is scalable, and its robustness is evidenced by the late-stage functionalization of various bioactive mols., which makes this reaction an attractive alternative in the synthesis of trifluoromethylthio- and selenoethers for pharmaceutical and agrochem. research and development. In the experiment, the researchers used many compounds, for example, 3-Iodophenol(cas: 626-02-8Product Details of 626-02-8)

3-Iodophenol(cas: 626-02-8) belongs to organic iodides. Organic iodides are used in veterinary products (Organic Iodide Powder) as a nutritional source of iodine.Product Details of 626-02-8 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.

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

Quality Control of (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthaleneOn March 1, 2021, Chen, Ching-Nung; Cheng, Wei-Min; Wang, Jian-Kai; Chao, Tzu-Hsuan; Cheng, Mu-Jeng; Liu, Rai-Shung published an article in Angewandte Chemie, International Edition. The article was 《Gold-catalyzed [3+2]-annulations of α-aryl diazoketones with the tetrasubstituted alkenes of cyclopentadienes: High stereoselectivity and enantioselectivity》. The article mentions the following:

This work reports gold-catalyzed [3+2]-annulations of α-diazo ketones with highly substituted cyclopentadienes, affording bicyclic 2,3-dihydrofurans with high regio- and stereoselectivity. The reactions highlights the first success of tetrasubstituted alkenes to undergo [3+2]-annulations with α-diazo carbonyls. The enantioselective annulations are also achieved with high enantioselectivity using chiral forms of gold and phosphoric acid. Our mechanistic anal. supports that cyclopentadienes serve as nucleophiles to attack gold carbenes at the more substituted alkenes, yielding gold enolates that complex with chiral phosphoric acid to enhance the enantioselectivity. In addition to this study using (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene, there are many other studies that have 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) was used in this study.

(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. Quality Control of (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene 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

Quality Control of (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthaleneOn October 13, 2021 ,《Bronsted Acid Catalyzed Stereoselective Polymerization of Vinyl Ethers》 was published in Journal of the American Chemical Society. The article was written by Knutson, Phil C.; Teator, Aaron J.; Varner, Travis P.; Kozuszek, Caleb T.; Jacky, Paige E.; Leibfarth, Frank A.. The article contains the following contents:

Isotactic poly(vinyl ether)s (PVEs) have recently been identified as a new class of semicrystalline thermoplastics with a valuable combination of mech. and interfacial properties. Currently, methods to synthesize isotactic PVEs are limited to strong Lewis acids that require a high catalyst loading and limit the accessible scope of monomer substrates for polymerization Here, we demonstrate the first Bronsted acid catalyzed stereoselective polymerization of vinyl ethers. A single-component imidodiphosphorimidate catalyst exhibits a sufficiently low pKa to initiate vinyl ether polymerization and acts as a chiral conjugate base to direct the stereochem. of monomer addition to the oxocarbenium ion reactive chain end. This Bronsted acid catalyzed stereoselective polymerization enabled an expanded substrate scope compared to previous methods, the use of chain transfer agents to lower catalyst loading, and the capability to recycle the catalyst for multiple polymerizations 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.Quality Control of (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene 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.

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

Recommanded Product: (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthaleneOn May 7, 1997 ,《Development of highly enantioselective polymeric catalysts using rigid and sterically regular chiral polybinaphthols》 appeared in Journal of the American Chemical Society. The author of the article were Huang, Wei-Sheng; Hu, Qiao-Sheng; Zheng, Xiao-Fan; Anderson, Julie; Pu, Lin. The article conveys some information:

A highly enantioselective polymeric catalyst based on sterically regular and rigid chiral polymers has been developed by systematically modifying the microenvironment of the catalytic centers in these polymers. These polymers are constructed by incorporating optically active 1,1′-bi-2-naphthol units into a rigid polymer chain, and are expected to have well-defined microenvironments around their catalytic sites when used in catalysis. The asym. reaction of aldehydes with diethylzinc catalyzed by the polybinaphthols to generate chiral alcs. has been studied. It was discovered that the polymer prepared by Suzuki coupling of the methoxymethyl group protected (R)-3,3′-diiodo-1,1′-bi-2-naphthol with 2,5-bis(hexyloxy)-1,4-phenylenediboronic acid, followed by hydrolysis, can produce chiral alcs. in up to 94% ee for the asym. reaction. It was also found that the high enantioselectivity is reproducible even when polymers prepared by different methods and with different mol. weights are used. The chiral polymer can be easily separated from the reaction mixture by simple precipitation and the recycled polymer shows the same enantioselectivity as the original polymer. This study provides a new direction to the design and synthesis of enantioselective polymeric catalysts. In the experiment, the researchers used (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene(cas: 189518-78-3Recommanded Product: (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. 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.Recommanded Product: (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene

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

In 2015,Chemistry – A European Journal included an article by Romanov-Michailidis, Fedor; Romanova-Michaelides, Maria; Pupier, Marion; Alexakis, Alexandre. Product Details of 189518-78-3. The article was titled 《Enantioselective Halogenative Semi-Pinacol Rearrangement: Extension of Substrate Scope and Mechanistic Investigations》. The information in the text is summarized as follows:

The present Full Paper article discloses a survey of our recent results obtained in the context of the enantioselective halogenation-initiated semi-pinacol rearrangement. Commencing with the fluorination/semi-pinacol reaction first and moving to the heavier halogens (bromine and iodine) second, the scope and limitations of the halogenative phase-transfer methodol. will be discussed and compared. An extension of the fluorination/semi-pinacol reaction to the ring-expansion of five-membered allylic cyclopentanols will be also described, as well as some preliminary results on substrates prone to desymmetrization will be given. Finally, the present manuscript will culminate with a detailed mechanistic investigation of the canonical fluorination/semi-pinacol reaction. Our mechanistic discussion will be based on in situ reaction progress monitoring, complemented with substituent effect, kinetic isotopic effect and non-linear behavior studies. After reading the article, we found that the author used (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene(cas: 189518-78-3Product Details of 189518-78-3)

(R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene(cas: 189518-78-3) belongs to organic iodides. Generally organic iodides can be divided into two classes of alkyl iodides and aryl iodides. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics.Product Details of 189518-78-3

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