Month: October 2022

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

In 2016,Huang, Huan-Ming; Procter, David J. published 《Radical-Radical Cyclization Cascades of Barbiturates Triggered by Electron-Transfer Reduction of Amide-Type Carbonyls》.Journal of the American Chemical Society published the findings.Name: 1,2-Diiodoethane The information in the text is summarized as follows:

Radical-radical cyclization cascades, triggered by single-electron transfer to amide-type carbonyls by SmI2-H2O, convert simple achiral barbiturates in one step to hemiaminal- or enamine-containing tricyclic scaffolds containing up to five contiguous stereocenters (including quaternary stereocenters). Furthermore, we describe the surprising beneficial effect of LiBr on the most challenging of the radical-radical cyclization cascades. An alternative fragmentation-radical cyclization sequence of related substrates allows access to bicyclic uracil derivatives The radical-radical cyclization process constitutes the first example of a radical cascade involving ET reduction of the amide carbonyl. Products of the cascade can be readily manipulated to give highly unusual and medicinally relevant bi- and tricyclic barbiturates. The results came from multiple reactions, including the reaction of 1,2-Diiodoethane(cas: 624-73-7Name: 1,2-Diiodoethane)

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.Name: 1,2-Diiodoethane

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

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,Chaminda Lakmal, Hetti Handi; Xu, Joanna Xiuzhu; Xu, Xue; Ahmed, Bassem; Fong, Christopher; Szalda, David J.; Ramig, Keith; Sygula, Andrzej; Webster, Charles Edwin; Zhang, Dongmao; Cui, Xin published 《Synthesis of C-Unsubstituted 1,2-Diazetidines and Their Ring-Opening Reactions via Selective N-N Bond Cleavage》.Journal of Organic Chemistry published the findings.Name: 1,2-Diiodoethane The information in the text is summarized as follows:

C-Unsubstituted 1,2-diazetidines, a rarely studied type of four-membered heterocyclic compounds, were synthesized through an operationally simple intermol. vicinal disubstitution reaction. 1,2-Diazetidine derivatives bearing various N-arylsulfonyl groups were readily accessed and studied by exptl. and computed Raman spectra. The ring-opening reaction of the diazetidine was explored and resulted in the identification of a selective N-N bond cleavage with thiols as nucleophiles, which stereoselectively produced a new class of N-sulfenylimine derivatives with C-aminomethyl groups. In addition to this study using 1,2-Diiodoethane, there are many other studies that have used 1,2-Diiodoethane(cas: 624-73-7Name: 1,2-Diiodoethane) was used in this study.

1,2-Diiodoethane(cas: 624-73-7) 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.Name: 1,2-Diiodoethane

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

In 2019,Journal of the American Chemical Society included an article by Swyka, Robert A.; Zhang, Wandi; Richardson, Jeffery; Ruble, J. Craig; Krische, Michael J.. Computed Properties of C7H7I. The article was titled 《Rhodium-Catalyzed Aldehyde Arylation via Formate-Mediated Transfer Hydrogenation: Beyond Metallic Reductants in Grignard/Nozaki-Hiyama-Kishi-Type Addition》. The information in the text is summarized as follows:

The first intermol. carbonyl arylations via transfer hydrogenative reductive coupling are described. Using rhodium catalysts modified by tBu2PMe, sodium formate-mediated reductive coupling of aryl iodides with aldehydes occurs in a chemoselective fashion in the presence of protic functional groups and lower halides. This work expands the emerging paradigm of transfer hydrogenative coupling as an alternative to pre-formed carbanions or metallic reductants in C=X addition The experimental part of the paper was very detailed, including the reaction process of 1-Iodo-4-methylbenzene(cas: 624-31-7Computed Properties 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.Computed Properties of C7H7I

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 2019,Research on Chemical Intermediates included an article by Nikpassand, Mohammad; Fekri, Leila Zare; Rahro, Parissa Naddaf. Reference of 4-Iodobenzaldehyde. The article was titled 《Catalyst-free grinding method: a new avenue for synthesis of 6-amino-3-methyl-4-aryl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile and DFT studies on the mechanistic pathway of this category of compounds》. The information in the text is summarized as follows:

An efficient, one-pot, catalyst-free grinding procedure for synthesis of 6-amino-3-methyl-4-aryl-1H-pyrazolo[3,4-b]pyridine-5-carbonitriles I [X = H, 3-Cl, 4-OMe, etc.] was reported. The condensation of substituted benzaldehydes, 3-amino-5-methylpyrazole and malononitrile according to a three-component reaction was investigated using d. functional theory (DFT) at B3LYP/6-311G level to explore the reaction mechanism. All the routes were studied, the structure of the intermediates was optimized and all the resp. transition states were found. The results of the calculations showed that the proposed mechanism relies on four intermediates. The results came from multiple reactions, including the reaction of 4-Iodobenzaldehyde(cas: 15164-44-0Reference of 4-Iodobenzaldehyde)

4-Iodobenzaldehyde(cas: 15164-44-0) is used in synthesis of 4-[2-(trimethylsilyl)ethynyl]benzaldehyde, 5,15-dimesityl-10-(3-[2-(trimethylsilyl)ethynyi]phenyl}-20-(4-iodophenyl)porphyrin, and 5,15-dimesityl-10-[3,5-bis{2-[4-(N,N’-difluoroboryl-1,9-dimethyidipyrrin-5-yl)-phenyl]ethynyl}phenyl]-20-(4-iodophenyl)porphyrin.Reference of 4-Iodobenzaldehyde

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

In 2019,Asian Journal of Organic Chemistry included an article by Padmavathi, Rayavarapu; Babu, Srinivasarao Arulananda. Synthetic Route of C7H7I. The article was titled 《Palladium-Catalyzed 8-Aminoquinoline-Aided sp2 δ-C-H Intramolecular Amidation/Annulation: A Route to Tricyclic Quinolones》. The information in the text is summarized as follows:

Systematic investigations of a Pd(II)-catalyzed, 8-aminoquinoline directing group (DG)-aided sp2 δ-C-H amidation (C-N bond formation) of different biaryl carboxamides were reported. Various biaryl carboxamides with suitably positioned sp2 δ-C-H bond with respect to the DG were assembled via β-C-H arylation and then they were subjected to Pd(II)-catalyzed sp2 δ-C-H intramol. amidation/annulation reactions. While the intramol. amidation of the sp2 δ-C-H bond of some carboxamides was not fruitful, several biaryl carboxamides underwent intramol. amidation of their sp2 δ-C-H bonds to afford various tricyclic quinolone motifs such as, phenanthridin-6(5H)-ones and thieno-/furo-/pyrrolo-[2,3-c]quinolin-4(5H)-ones. The assembly of the required biaryl carboxamides possessing the sp2 δ-C-H bond via the β-C-H arylation and the successive intramol. amidation (C-N bond formation) of the resulting biaryl carboxamides were also performed in one-pot reaction conditions to afford tricyclic quinolones. In addition to this study using 1-Iodo-4-methylbenzene, there are many other studies that have used 1-Iodo-4-methylbenzene(cas: 624-31-7Synthetic Route of C7H7I) was used in this study.

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

《A novel magnetically recoverable palladium nanocatalyst containing organoselenium ligand for the synthesis of biaryls via Suzuki-Miyaura coupling reaction》 was published in Journal of Physics and Chemistry of Solids in 2020. These research results belong to Rangraz, Yalda; Nemati, Firouzeh; Elhampour, Ali. Electric Literature of C7H7I The article mentions the following:

In the present work, a novel heterogeneous catalytic system involving palladium(II) complex as moisture- and air-stable organoselenium ligand supported on Fe3O4 nanoparticles modified by SiO2/azidopropyltrimethoxy silane was designed, synthesized and characterized using various physicochem. methods inclusive of VSM, EDX, FE-SEM, TG, XRD, and FT-IR spectroscopy. The catalytic activity of the synthesized magnetic nanocatalyst which named Fe3O4@SiO2-T-Se/Pd(II) was evaluated in Suzuki-Miyaura coupling reactions for the preparation of corresponding biaryls RR1 (R = Ph, 1-naphthyl, 2-thiophenyl, etc.; R1 = Ph, 4-fluorophenyl, 4-methylphenyl) using diverse aryl halides RX (X = I, Br) and arylboronic acids R1B(OH)2. The mild reaction conditions, variety of substrate scope, good yield, low reaction time, high stability, utilization of organoselenium compound as an air and moisture insensitive ligand and its immobilization on solid support, and more importantly effortless recovery and recyclability of the catalyst up to seven consecutive runs with no remarkable change in its activity are some of the interesting features of this protocol that makes it more beneficial from both industrial and environmental points of view. After reading the article, we found that the author used 1-Iodo-4-methylbenzene(cas: 624-31-7Electric Literature 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.Electric Literature of C7H7I

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