Author: Jessica.F

Product Details of 90-14-2In 2019 ,《One-Pot and Reducible-Functional-Group-Tolerant Synthesis of α-Aryl- and α-Heteroaryl-α-Trifluoromethyl Alcohols via Tandem Trifluoroacetylation and MPV Type Reduction》 was published in European Journal of Organic Chemistry. The article was written by Funabiki, Kazumasa; Hayakawa, Ayaka; Kani, Ryunosuke; Inuzuka, Toshiyasu; Kubota, Yashuhiro. The article contains the following contents:

We have developed a new one-pot synthesis of α-aryl- and α-heteroaryl-α-trifluoromethyl alcs. carrying not only arenes with electron-withdrawing groups but also electron-deficient nitrogen-containing heteroarenes, which are of increasing interest because these compounds are some of the most important units in current fluorine-containing inhibitors or antagonists. This new method includes three tandem reactions in a one-pot synthesis: (1) the in situ generation of functionalized aromatic and electron-deficient heteroaromatic Grignard reagents, (2) trifluoroacetylation of the generated Grignard reagents with diphenylmethyl trifluoroacetate, and (3) successive Meerwein-Ponndorf-Verley type reduction It offers several advantages, including no need for expensive transition metals and gaseous trifluoromethylating reagents, toleration of not only reducible functional groups on the aryl groups but also electron-deficient nitrogen-containing heterocycles, easy scalability, and the ability to suppress the formation of the bis-aldol product as a byproduct by changing the ester moiety of the trifluoroacetate from an iso-Pr to a diphenylmethyl group. The results came from multiple reactions, including the reaction of 1-Iodonaphthalene(cas: 90-14-2Product Details of 90-14-2)

1-Iodonaphthalene(cas: 90-14-2) 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 90-14-2

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

《Direct Synthesis of Tri-/Difluoromethyl Ketones from Carboxylic Acids by Cross-Coupling with Acyloxyphosphonium Ions》 was written by Ispizua-Rodriguez, Xanath; Munoz, Socrates B.; Krishnamurti, Vinayak; Mathew, Thomas; Prakash, G. K. S.. Recommanded Product: 2-Iodobenzoic acidThis research focused ontrifluoromethyl ketone preparation chemoselective; carboxylic acid trifluoromethyltrimethylsilane cross coupling reaction; difluoromethyl ketone preparation chemoselective; dimethylpropyleneurea zinc difluoromethyl carboxylic acid cross coupling reaction; TMSCF3; acyloxyphosphonium; carboxylic acids; copper; difluoromethyl ketones; trifluoromethyl ketones. The article conveys some information:

A simple and straightforward approach to the synthesis of trifluoromethyl and difluoromethyl ketones RC(O)CF3 [R = naphth-2-yl, benzyl, (Z)-cycloundecen-2-yl, etc.] and RC(O)CF2H from widely available carboxylic acids RC(O)OH is disclosed. The transformation utilizes an acyloxyphosphonium ion as the active electrophile, conveniently generated in situ from the carboxylic acid substrate by using commodity chems. The utility of the reaction system is exemplified by its chemoselectivity, with tolerance to a variety of important functional groups. The late-stage functionalization of carboxylic acid active pharmaceutical ingredients and pharmaceutically relevant compounds is also discussed. The results came from multiple reactions, including the reaction of 2-Iodobenzoic acid(cas: 88-67-5Recommanded Product: 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.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.Recommanded Product: 2-Iodobenzoic acid

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

《Electrochemical Vicinal Difluorination of Alkenes: Scalable and Amenable to Electron-rich Substrates》 was written by Doobary, Sayad; Sedikides, Alexi T.; Caldora, Henry P.; Poole, Darren L.; Lennox, Alastair J. J.. HPLC of Formula: 624-31-7This research focused onvicinal difluoroalkane preparation difluorination unactivated alkene hypervalent iodine mediator; electrochem difluorination unactivated alkene hypervalent iodine mediator; electrochemistry; fluorination; green chemistry; hypervalent iodine; oxidation. The article conveys some information:

Fluorinated alkyl groups are important motifs in bioactive compounds, pos. influencing pharmacokinetics, potency and conformation. The oxidative difluorination of alkenes represents an important strategy for their preparation, yet current methods are limited in their alkene-types and tolerance of electron-rich, readily oxidized functionalities, as well as in their safety and scalability. Herein, we report a method for the difluorination of a number of unactivated alkene-types that is tolerant of electron-rich functionality, giving products that are otherwise unattainable. Key to success is the electrochem. generation of a hypervalent iodine mediator using an “”ex-cell”” approach, which avoids oxidative substrate decomposition The more sustainable conditions give good to excellent yields in up to decagram scales. Of note, when handling HF reagents, personal protection is of utmost importance. In the experimental materials used by the author, we found 1-Iodo-4-methylbenzene(cas: 624-31-7HPLC of Formula: 624-31-7)

1-Iodo-4-methylbenzene(cas: 624-31-7) is used in wide range of medicals industrial applications as well as in pharmaceutical intermediates, polarizing films for Liquid Crystal Display (LCD) chemicals.HPLC of Formula: 624-31-7

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

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