Tag: 300-400

《Ligand-Promoted meta-C-H Functionalization of Benzylamines》 was published in Angewandte Chemie, International Edition in 2017. These research results belong to Wang, Peng; Farmer, Marcus E.; Yu, Jin-Quan. Quality Control of 2-Chloro-5-iodo-3-(trifluoromethyl)pyridine The article mentions the following:

Meta-C-H functionalization of benzylamines has been developed using a PdII/transient mediator strategy. Using 2-pyridone ligands and 2-carbomethoxynorbornene (NBE-CO2Me) as the mediator, arylation, amination, and chlorination of benzylamines are realized. This protocol features a broad substrate scope and is compatible with heterocylic coupling partners. Moreover, the loading of the Pd can be lowered to 2.5 mol % by using the optimal ligand. In addition to this study using 2-Chloro-5-iodo-3-(trifluoromethyl)pyridine, there are many other studies that have used 2-Chloro-5-iodo-3-(trifluoromethyl)pyridine(cas: 887707-25-7Quality Control of 2-Chloro-5-iodo-3-(trifluoromethyl)pyridine) was used in this study.

2-Chloro-5-iodo-3-(trifluoromethyl)pyridine(cas: 887707-25-7) belongs to pyridine. Pyridine-based materials are valued for their optical and physical properties as well as their medical potential. Additionally, pyridine-based natural products continue to be discovered and studied for their properties and to understand their biosynthesis.Quality Control of 2-Chloro-5-iodo-3-(trifluoromethyl)pyridine

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

In 2018,Angewandte Chemie, International Edition included an article by Cheng, Ying; Mueck-Lichtenfeld, Christian; Studer, Armido. Computed Properties of C10H18INO2. The article was titled 《Metal-Free Radical Borylation of Alkyl and Aryl Iodides》. The information in the text is summarized as follows:

A metal-free radical borylation of alkyl and aryl iodides with bis(catecholato)diboron (B2cat2) as the B source under mild conditions is introduced. The borylation reaction is operationally easy to conduct and shows high functional group tolerance and broad substrate scope. Radical clock experiments and d. functional theory calculations provide insights into the mechanism and rate constants for C-radical borylation with B2cat2 are disclosed. 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

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

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

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

Synthetic Route of C10H18INO2In 2019 ,《Ligand-Controlled Regiodivergent Hydroalkylation of Pyrrolines》 appeared in Angewandte Chemie, International Edition. The author of the article were Qian, Deyun; Hu, Xile. The article conveys some information:

Two series of C-alkylated pyrrolidines I [R = Boc, Cbz; R1 = i-Pr, cyclopentyl, indol-1-yl, etc.] and II [R2 = CO2Ph, Boc, Cbz; R3 = cyclohexyl, (CH2)3Ph, 2-thienyl, etc.] were synthesized via ligand controlled nickel-catalyzed regiodivergent hydroalkylation of 3-pyrrolines with alkyl/aryl halides. This method demonstrated broad scope and high functional-group tolerance and could be applied in late-stage functionalizations. In the experiment, the researchers used many compounds, for example, tert-Butyl 4-iodopiperidine-1-carboxylate(cas: 301673-14-3Synthetic Route of C10H18INO2)

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

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

In 2019,Journal of the American Chemical Society included an article by Hazra, Avijit; Chen, Jason; Lalic, Gojko. Recommanded Product: tert-Butyl 4-iodopiperidine-1-carboxylate. The article was titled 《Stereospecific Synthesis of E-Alkenes through Anti-Markovnikov Hydroalkylation of Terminal Alkynes》. The information in the text is summarized as follows:

The authors have developed a method for stereospecific synthesis of E-alkenes from terminal alkynes and alkyl iodides. The hydroalkylation reaction is enabled by a cooperative action of copper and nickel catalysts and proceeds with excellent anti-Markovnikov selectivity. The authors demonstrate the broad scope of the reaction, which can be accomplished in the presence of esters, nitriles, aryl bromides, ethers, alkyl chlorides, anilines, and a wide range of nitrogen-containing heteroaromatic compounds Mechanistic studies provide evidence that the copper catalyst activates the alkyne by hydrocupration, which controls both the regio- and diastereoselectivity of the overall reaction. The nickel catalyst activates the alkyl iodide and promotes cross coupling with the alkenyl copper intermediate. 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: 301673-14-3Recommanded Product: tert-Butyl 4-iodopiperidine-1-carboxylate) 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.Recommanded Product: tert-Butyl 4-iodopiperidine-1-carboxylate

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

In 2018,Chen, Yi-Hung; Grassl, Simon; Knochel, Paul published 《Cobalt-Catalyzed Electrophilic Amination of Aryl- and Heteroarylzinc Pivalates with N-Hydroxylamine Benzoates》.Angewandte Chemie, International Edition published the findings.Category: iodides-buliding-blocks The information in the text is summarized as follows:

Aryl- and heteroarylzinc pivalates can be aminated with O-benzoylhydroxylamines at 25° within 2-4 h in the presence of 2.5-5.0% CoCl2·2LiCl to furnish the corresponding tertiary arylated or heteroarylated amines in good yields. This electrophilic amination also provides access to diarylamines and aryl(heteroaryl)amines. A new tuberculosis drug candidate (Q203) was prepared in six steps and 56% overall yield by using this cobalt-catalyzed amination as the key step. In the experiment, the researchers used tert-Butyl 4-iodopiperidine-1-carboxylate(cas: 301673-14-3Category: iodides-buliding-blocks)

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.Category: iodides-buliding-blocks

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

In 2018,Cheng, Li-Jie; Islam, Shahidul M.; Mankad, Neal P. published 《Synthesis of Allylic Alcohols via Cu-Catalyzed Hydrocarbonylative Coupling of Alkynes with Alkyl Halides》.Journal of the American Chemical Society published the findings.Reference of tert-Butyl 4-iodopiperidine-1-carboxylate The information in the text is summarized as follows:

We have developed a modular procedure to synthesize allylic alcs. from tertiary, secondary, and primary alkyl halides and alkynes via a Cu-catalyzed hydrocarbonylative coupling and 1,2-reduction tandem sequence. The use of tertiary alkyl halides as electrophiles was found to enable the synthesis of various allylic alcs. bearing α-quaternary carbon centers in good yield with high 1,2-reduction selectivity. Mechanistic studies that suggested a different pathway was operative with tertiary alkyl halides compared with primary and secondary alkyl halides for generating the key copper(III) oxidative adduct. For tertiary electrophiles, an acyl halide likely forms via radical atom transfer carbonylation. The preference for 1,2-reduction over 1,4-reduction of α,β-unsaturated ketones bearing tertiary substituents was rationalized using d. functional theory transition state anal. On the basis of this computational model, the coupling method was extended to primary and secondary alkyl iodide electrophiles by using internal alkynes with aryl substituents, providing trisubstituted allylic alcs. in high yield with good regioselectivity. The experimental process involved the reaction of 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

Synthetic Route of C6H2ClF3INOn June 1, 2020, Xiao, Li-Jun; Hong, Kai; Luo, Fan; Hu, Liang; Ewing, William R.; Yeung, Kap-Sun; Yu, Jin-Quan published an article in Angewandte Chemie, International Edition. The article was 《PdII-Catalyzed Enantioselective C(sp3)-H Arylation of Cyclobutyl Ketones Using a Chiral Transient Directing Group》. The article mentions the following:

In the presence of Pd(OAc)2, 3-nitro-5-trifluoromethyl-2-pyridone, and D-valine as a transient directing group reagent, cyclobutyl ketones such as I (R = H) underwent regioselective, diastereoselective, and enantioselective arylation with aryl iodides R1I (R1 = 4-MeO2CC6H4, 4-O2NC6H4, 4-MeCOC6H4, 4-NCC6H4, 4-F3CC6H4, 3-O2NC6H4, 3-PhCOC6H4, 3,4,5-F3C6H2, 3,5-Br2C6H3, 3-Br-5-ClC6H3, 4-Me-3-O2NC6H3, 2-Br-5-FC6H3, 6-F-3-pyridinyl, 2-F3C-4-pyridinyl, 6-Cl-5-F3C-3-pyridinyl, 6-Br-3-pyridinyl, 2,6-F2-4-pyridinyl, 2,6-F2-3-pyridinyl, 2,6-Cl2-4-pyridinyl, 5-acetyl-2-thienyl) to yield arylcyclobutyl ketones such as I (R = 4-MeO2CC6H4, 4-O2NC6H4, 4-MeCOC6H4, 4-NCC6H4, 4-F3CC6H4, 3-O2NC6H4, 3-PhCOC6H4, 3,4,5-F3C6H2, 3,5-Br2C6H3, 3-Br-5-ClC6H3, 4-Me-3-O2NC6H3, 2-Br-5-FC6H3, 6-F-3-pyridinyl, 2-F3C-4-pyridinyl, 6-Cl-5-F3C-3-pyridinyl, 6-Br-3-pyridinyl, 2,6-F2-4-pyridinyl, 2,6-F2-3-pyridinyl, 2,6-Cl2-4-pyridinyl, 5-acetyl-2-thienyl). In the presence of either L-valine as a transient directing group reagent or when silver trifluoroacetate, acetate, carbonate, or oxide were used as bases, enantiomeric arylcyclobutyl ketones were formed. A sequential diarylation was performed to yield diastereomeric diarylcyclobutyl ketones enantioselectively. In the experiment, the researchers used 2-Chloro-5-iodo-3-(trifluoromethyl)pyridine(cas: 887707-25-7Synthetic Route of C6H2ClF3IN)

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.Synthetic Route of C6H2ClF3IN

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