Tag: 200-300

Chen, Mengyuan; Liang, Yuchen; Dong, Taotao; Liang, Weijian; Liu, Yanping; Zhang, Yage; Huang, Xin; Kong, Lichun; Wang, Zhi-Xiang; Peng, Bo published their research in Angewandte Chemie, International Edition in 2021. The article was titled 《Z-Selective α-Arylation of α,β-Unsaturated Nitriles via [3,3]-Sigmatropic Rearrangement》.Category: iodides-buliding-blocks The article contains the following contents:

The Morita-Baylis-Hillman (MBH) reaction and [3, 3]-sigmatropic rearrangement are two paradigms in organic synthesis. We have merged the two types of reactions to achieve [3,3]-rearrangement of aryl sulfoxides with α,β-unsaturated nitriles. The reaction was achieved by sequentially treating both coupling partners with electrophilic activator (Tf2O) and base, offering an effective approach to prepare synthetically versatile α-aryl α,β-unsaturated nitriles with Z-selectivity through direct α-C-H arylation of unmodified α,β-unsaturated nitriles. The control experiments and DFT calculations support a four-stage reaction sequence, including the assembly of Tf2O activated aryl sulfoxide with α,β-unsaturated nitrile, MBH-like Lewis base addition, [3,3]-rearrangement, and E1cB-elimination. Among these stages, the Lewis base addition is diastereoselective and E1cB-elimination is cis-selective, which could account for the remarkable Z-selectivity of the reaction. In the experiment, the researchers used many compounds, for example, Trimethylsulfoxonium iodide(cas: 1774-47-6Category: iodides-buliding-blocks)

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.Category: iodides-buliding-blocks

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

Appa, Rama Moorthy; Ramesh Naidu, Bandameeda; Venkateswarlu, Derangula; Hanafiah, Marlia M.; Lakkaboyana, Sivarama Krishna; Lakshmidevi, Jangam; Venkateswarlu, Katta published their research in Green Chemistry Letters and Reviews in 2021. The article was titled 《Water extract of pomegranate ash-I2 as sustainable system for external oxidant/metal/catalyst-free oxidative iodination of (hetero)arenes》.HPLC of Formula: 63069-48-7 The article contains the following contents:

An added oxidant/metal/catalyst/additive and problematic solvent-free versatile and straightforward protocol was reported for the synthesis of aryl iodides (AIs) using mol. iodine (I2) in water extract of pomegranate ash (WEPA). These transformations were performed at room temperature (rt) and the reactions took place in 5-20 min to give 83-99% yields of aryl iodides. WEPA was characterized by using XPS, EDX, XRF, XRD and FTIR anal. and a plausible mechanism had been established based on these anal. along with some control experiments Further, the products were purified by recrystallization technique. This work with intrinsic sustainability, high substrate feasibility, utilization of biorenewable catalystytic media, ease of execution and separation of products, and added oxidant/catalyst/metal and additive-free conditions might became one among the forefront sustainable procedures in making aryl iodides. The use of waste-derived WEPA as catalystytic media for this iodination was the novelty of this method and might be used these aryl iodides for further in-process transformations (e.g. cross-couplings, nucleophilic reactions, etc.) to access fine chems. In the experiment, the researchers used many compounds, for example, 4-Chloro-2-iodoaniline(cas: 63069-48-7HPLC of Formula: 63069-48-7)

4-Chloro-2-iodoaniline(cas: 63069-48-7) belongs to anime. Aniline, ethanolamines, and several other amines are major industrial commodities used in making rubber, dyes, pharmaceuticals, and synthetic resins and fibres and for a host of other applications. Most of the numerous methods for the preparation of amines may be broadly divided into two groups: (1) chemical reduction (replacement of oxygen with hydrogen atoms in the molecule) of members of several other classes of organic nitrogen compounds and (2) reactions of ammonia or amines with organic compounds.HPLC of Formula: 63069-48-7

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

《Pd/Cu-Catalyzed Enantioselective Sequential Heck/Sonogashira Coupling: Asymmetric Synthesis of Oxindoles Containing Trifluoromethylated Quaternary Stereogenic Centers》 was written by Bai, Xingfeng; Wu, Caizhi; Ge, Shaozhong; Lu, Yixin. Recommanded Product: 4-Chloro-2-iodoaniline And the article was included in Angewandte Chemie, International Edition in 2020. The article conveys some information:

An asym. palladium and copper co-catalyzed Heck/Sonogashira reaction between o-iodoacrylanilides and terminal alkynes to synthesize chiral oxindoles was developed. In particular, a wide range of CF3-substituted o-iodoacrylanilides reacted with terminal alkynes, affording the corresponding chiral oxindoles containing trifluoromethylated quaternary stereogenic centers in high yields with excellent enantioselectivities (94-98% ee). This asym. Heck/Sonogashira reaction provides a general approach to access oxindole derivatives containing quaternary stereogenic centers including CF3-substituted ones. In addition to this study using 4-Chloro-2-iodoaniline, there are many other studies that have used 4-Chloro-2-iodoaniline(cas: 63069-48-7Recommanded Product: 4-Chloro-2-iodoaniline) was used in this study.

4-Chloro-2-iodoaniline(cas: 63069-48-7) belongs to anime. Examples of direct uses of amines and their salts are as corrosion inhibitors in boilers and in lubricating oils (morpholine), as antioxidants for rubber and roofing asphalt (diarylamines), as stabilizers for cellulose nitrate explosives (diphenylamine), as protectants against damage from gamma radiation (diarylamines), as developers in photography (aromatic diamines), as flotation agents in mining, as anticling and waterproofing agents for textiles, as fabric softeners, in paper coating, and for solubilizing herbicides.Recommanded Product: 4-Chloro-2-iodoaniline

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

《Evidence for Photocatalyst Involvement in Oxidative Additions of Nickel-Catalyzed Carboxylate O-Arylations》 was published in Journal of the American Chemical Society in 2020. These research results belong to Malik, Jamal A.; Madani, Amiera; Pieber, Bartholomaeus; Seeberger, Peter H.. Synthetic Route of C7H7I The article mentions the following:

Dual photocatalysis and nickel catalysis can effect cross-coupling under mild conditions, but little is known about the in situ kinetics of this class of reactions. We report a comprehensive kinetic examination of a model carboxylate O-arylation, comparing a state-of-the-art homogeneous photocatalyst (Ir(ppy)3) with a competitive heterogeneous photocatalyst (graphitic carbon nitride). Exptl. conditions were adjusted such that the nickel catalytic cycle is saturated with excited photocatalyst. This approach was designed to remove the role of the photocatalyst, by which only the intrinsic behaviors of the nickel catalytic cycles are observed The two reactions did not display identical kinetics. Ir(ppy)3 deactivates the nickel catalytic cycle and creates more dehalogenated side product. Kinetic data for the reaction using Ir(ppy)3 supports a turnover-limiting reductive elimination. Graphitic carbon nitride gave higher selectivity, even at high photocatalyst-to-nickel ratios. The heterogeneous reaction also showed a rate dependence on aryl halide, indicating that oxidative addition plays a role in rate determination The results argue against the current mechanistic hypothesis, which states that the photocatalyst is only involved to trigger reductive elimination. The experimental process involved the reaction of 1-Iodo-4-methylbenzene(cas: 624-31-7Synthetic Route of C7H7I)

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.Synthetic Route of C7H7I

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

《One-Pot Synthesis of 1-[(Triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one (TIPS-EBX): Process Safety Assessment and Impact of Impurities on Product Stability》 was published in Organic Process Research & Development in 2020. These research results belong to Hari, Durga Prasad; Caramenti, Paola; Schouwey, Lionel; Chang, Miyeon; Nicolai, Stefano; Bachert, Donald; Wright, Timothy; Orella, Chuck; Waser, Jerome. Product Details of 88-67-5 The article mentions the following:

The hypervalent iodine reagent I, 1-[(TriIsoPropylSilyl)Ethynyl]-1,2-BenziodoXol-3(1H)-one (TIPS-EBX) is among the most useful electrophilic and somophilic alkynylation reagents. Herein, we report a new synthetic protocol to access this reagent in one step from standard com. available reagents. Thermal anal. of the synthesis procedure showed only weak exotherms. The compound could be obtained with high purity and stability using this new protocol, but care had to be taken to remove tosylate salts impurities, as they led to a lower thermal stability. TIPS-EBX synthesized using the new procedure displayed no shock sensitivity. In the experiment, the researchers used 2-Iodobenzoic acid(cas: 88-67-5Product Details of 88-67-5)

2-Iodobenzoic acid(cas: 88-67-5) 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 88-67-5

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

《Spatial Anion Control on Palladium for Mild C-H Arylation of Arenes》 was published in Journal of the American Chemical Society in 2020. These research results belong to Dhankhar, Jyoti; Gonzalez-Fernandez, Elisa; Dong, Chao-Chen; Mukhopadhyay, Tufan K.; Linden, Anthony; Coric, Ilija. SDS of cas: 625-99-0 The article mentions the following:

C-H arylation of arenes without the use of directing groups is a challenge, even for simple mols., such as benzene. We describe spatial anion control as a concept for the design of catalytic sites for C-H bond activation, thereby enabling nondirected C-H arylation of arenes at ambient temperature The mild conditions enable late-stage structural diversification of biol. relevant small mols., and site-selectivity complementary to that obtained with other methods of arene functionalization can be achieved. These results reveal the potential of spatial anion control in transition-metal catalysis for the functionalization of C-H bonds under mild conditions. In the experiment, the researchers used many compounds, for example, 1-Chloro-3-iodobenzene(cas: 625-99-0SDS of cas: 625-99-0)

1-Chloro-3-iodobenzene(cas: 625-99-0) belongs to organic iodides.SDS of cas: 625-99-0 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

In 2019,Journal of the American Chemical Society included an article by Goswami, Abir; Paululat, Thomas; Schmittel, Michael. Product Details of 15854-87-2. The article was titled 《Switching Dual Catalysis without Molecular Switch: Using A Multicomponent Information System for Reversible Reconfiguration of Catalytic Machinery》. The information in the text is summarized as follows:

Different from the current paradigms of chem., a switchable catalytic system is presented that does not rely on a mol. switch in different toggling states but on a smart seven-component mixture that manages the reversible ON/OFF regulation of two catalytic processes. Hereunto, the workflow of two multicomponent rotary catalytic machineries was interlinked by the simultaneous shuffling of two components (metal and ligand) requiring perfect signaling in a 13-component system (see Movie 1). This network underwent reversible switching over three cycles as demonstrated by 1H NMR, UV-visible, and fluorescence spectroscopies and electrospray ionization mass spectrometry. Addition and removal of zinc(II) ions trigger three distinct events in parallel: the (i) mutually dependent self-assembly of three-component nanorotors and two-component reservoirs by resorting components, (ii) toggling between vastly different rotational exchange rates in the self-assembled rotors that directly affect catalysis, and (iii) toggling between two diverse catalytic reactions in a fully reproducible manner. Because of this information system, the concentrations of free aza-crown ether 7 and its complex with copper(I), i.e., [Cu(7)]+, which represent the effective catalysts, are up- and downregulated in a manner to alternately switch ON/OFF a catalytic conjugate addition and a click reaction. After reading the article, we found that the author used 4-Iodopyridine(cas: 15854-87-2Product Details of 15854-87-2)

4-Iodopyridine(cas: 15854-87-2) belongs to pyridine. Pyridines are often used as catalysts or reagents; particular notice has been paid recently to how pyridine coordinates to metal centers enabling a wide range of valuable reactions. Product Details of 15854-87-2

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

In 2019,Journal of Organic Chemistry included an article by Aleman-Ponce de Leon, Diego; Sanchez-Chavez, Anahi C.; Polindara-Garcia, Luis A.. Synthetic Route of C6H4ClI. The article was titled 《Pd-Mediated γ-C(sp3)-H Bond Activation in Ammonia-Ugi 4-CR Adducts by Using Picolinamide as Directing Group》. The information in the text is summarized as follows:

The development of a novel protocol for the fast introduction of the picolinamide directing group in aliphatic ketones by using the ammonia-Ugi 4-CR reaction and the subsequent evaluation of the Pd-mediated γ-C(sp3)-H bond activation is described. The methodol. allows the efficient construction of a series of γ-arylated α-aminoamides bearing a congested carbon in two steps.1-Chloro-3-iodobenzene(cas: 625-99-0Synthetic Route of C6H4ClI) was used in this study.

1-Chloro-3-iodobenzene(cas: 625-99-0) belongs to organic iodides. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.Synthetic Route of C6H4ClIIodo 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

In 2016,Fischer, Stefan; Huwyler, Nikolas; Wolfrum, Susanne; Carreira, Erick M. published 《Synthesis and Biological Evaluation of Bromo- and Fluorodanicalipin A》.Angewandte Chemie, International Edition published the findings.Related Products of 624-73-7 The information in the text is summarized as follows:

We disclose the syntheses of (+)-bromodanicalipin A as well as (±)-fluorodanicalipin A. The relative configuration and ground-state conformation in solution of both mols. was secured by J-based configuration anal. which revealed that these are identical to natural danicalipin A. Furthermore, preliminary toxicol. investigations suggest that the adverse effect of danicalipin A may be due to the lipophilicity of the halogens. The results came from multiple reactions, including the reaction of 1,2-Diiodoethane(cas: 624-73-7Related Products 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.Related Products of 624-73-7

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

The author of 《Synthesis of Pyrimido[5′,4′:4,5]pyrrolo[1,2-f]phenanthridines by a One-Pot C-N-Coupling/Hydroamination/C-H-Arylation Sequence》 were Ngo, Nghia Pham; Ali Salman, Ghazwan; Belattar, Nadjah; Tuan, Thanh Dang; Ehlers, Peter; Langer, Peter. And the article was published in European Journal of Organic Chemistry in 2017. Product Details of 83410-16-6 The author mentioned the following in the article:

A modular and atom-economic synthetic pathway towards 11,13-dimethylpyrimido[5′,4′:4,5]pyrrolo[1,2-f]phenanthridines is described. The protocol features a chemoselective Sonogashira reaction of a 4,5-dihalopyrimidine followed by a domino C-N coupling/hydroamination and C-H arylation that can be achieved in a one-pot process. The yields vary from moderate to good.4-Chloro-5-iodo-2,6-dimethylpyrimidine(cas: 83410-16-6Product Details of 83410-16-6) was used in this study.

4-Chloro-5-iodo-2,6-dimethylpyrimidine(cas: 83410-16-6) 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.Product Details of 83410-16-6

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