Month: October 2022

Category: iodides-buliding-blocksOn November 9, 2016 ,《Pd-Catalyzed γ-C(sp3)-H Arylation of Free Amines Using a Transient Directing Group》 appeared in Journal of the American Chemical Society. The author of the article were Wu, Yongwei; Chen, Yan-Qiao; Liu, Tao; Eastgate, Martin D.; Yu, Jin-Quan. The article conveys some information:

In the presence of Pd(OAc)2 and using AgO2CCF3 and H2O as additives in AcOH/(F3C)2CHOH, 20 mol% 2-hydroxy-3-pyridinecarboxaldehyde forms a transient directing group with primary alkylamines such as cyclohexylamine which directs their regioselective (and in some cases, diastereoselective) arylation reactions with aryl and heteroaryl iodides such as RI followed by Boc protection to yield Boc-protected γ-aryl amines such as I in 43-91% yields (in most cases with high selectivity for the monoarylated products). Importantly, the catalyst and the directing group loading can be lowered to 2% and 4% resp., thus demonstrating high efficiency of this newly designed transient directing group. A tetrahydronaphthyridine II was prepared from 2-methyl-1-butanamine and 2-fluoro-3-iodopyridine by a one-pot directed arylation and cyclization. The experimental process involved the reaction of 2-Chloro-5-iodo-3-(trifluoromethyl)pyridine(cas: 887707-25-7Category: iodides-buliding-blocks)

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.Category: iodides-buliding-blocks

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

Application In Synthesis of 2-Chloro-5-iodo-3-(trifluoromethyl)pyridineOn May 4, 2020 ,《Ligand-Enabled β-Methylene C(sp3)-H Arylation of Masked Aliphatic Alcohols》 appeared in Angewandte Chemie, International Edition. The author of the article were Xia, Guoqin; Zhuang, Zhe; Liu, Luo-Yan; Schreiber, Stuart L.; Melillo, Bruno; Yu, Jin-Quan. The article conveys some information:

Despite recent advances, reactivity and site-selectivity remain significant obstacles for the practical application of C(sp3)-H bond functionalization methods. Here, we describe a system that combines a salicylic-aldehyde-derived L,X-type directing group with an electron-deficient 2-pyridone ligand to enable the β-methylene C(sp3)-H arylation of aliphatic alcs., which has not been possible previously. Notably, this protocol is compatible with heterocycles embedded in both alc. substrates and aryl coupling partners. A site- and stereo-specific annulation of dihydrocholesterol and the synthesis of a key intermediate of englitazone illustrate the practicality of this method. After reading the article, we found that the author used 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

Doi, Yasuhiro; Chiba, Junya; Morikawa, Tomoyuki; Inouye, Masahiko published an article in Journal of the American Chemical Society. The title of the article was 《Artificial DNA Made Exclusively of Nonnatural C-Nucleosides with Four Types of Nonnatural Bases》.Safety of 2-Amino-5-iodopyrimidin-4(1H)-one The author mentioned the following in the article:

A new class of DNA-like oligomers made exclusively of nonnatural, stable C-nucleosides is described. The nucleosides comprise four types of nonnatural bases attached to a deoxyribose through an acetylene bond with the β-configuration. The artificial DNA forms right-handed duplexes and triplexes with the complementary artificial DNA. The hybridization occurs spontaneously and sequence-selectively, and the resulting duplexes have thermal stabilities very close to those of natural duplexes. The artificial DNA might be applied to a future extracellular genetic system with information storage and amplifiable abilities. In addition to this study using 2-Amino-5-iodopyrimidin-4(1H)-one, there are many other studies that have used 2-Amino-5-iodopyrimidin-4(1H)-one(cas: 3993-79-1Safety of 2-Amino-5-iodopyrimidin-4(1H)-one) was used in this study.

2-Amino-5-iodopyrimidin-4(1H)-one(cas: 3993-79-1) 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.Safety of 2-Amino-5-iodopyrimidin-4(1H)-one

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

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

In 2018,Jiao, Zhiwei; Lim, Li Hui; Hirao, Hajime; Zhou, Jianrong Steve published 《Palladium-Catalyzed para-Selective Alkylation of Electron-Deficient Arenes》.Angewandte Chemie, International Edition published the findings.Reference of tert-Butyl 4-iodopiperidine-1-carboxylate The information in the text is summarized as follows:

Intermol. alkylations of electron-deficient arenes proceed with good para selectivity. Palladium catalysts were used to generate nucleophilic alkyl radicals from alkyl halides, which then directly add onto the arenes. The arene scope and the site of alkylation are opposite to those of classical Friedel-Crafts alkylations, which prefer electron-rich systems. In the part of experimental materials, we found many familiar compounds, such as tert-Butyl 4-iodopiperidine-1-carboxylate(cas: 301673-14-3Reference of tert-Butyl 4-iodopiperidine-1-carboxylate)

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.Reference of tert-Butyl 4-iodopiperidine-1-carboxylate

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 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

《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

《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