Tag: 200-300

He, Yu-Ping; Cao, Jian; Wu, Hua; Wang, Qian; Zhu, Jieping published their research in Angewandte Chemie, International Edition in 2021. The article was titled 《Catalytic Enantioselective Aminopalladation-Heck Cascade》.Recommanded Product: 4-Chloro-2-iodoaniline The article contains the following contents:

Domino processes initiated by intramol. nucleopalladation of alkynes have been developed into powerful synthetic tools for the synthesis of functionalized heterocycles. However, a catalytic enantioselective version of this class of reactions remains scarce. We report herein that reaction of 2-alkynylanilines with prochiral cyclopentenes in the presence of a catalytic amount of Pd(OAc)2, a chiral bidentate pyrox ligand and O2 as terminal oxidant affords the structurally diverse indole-cyclopentene conjugates, e.g., I, bearing two stereocenters in a highly diastereo- and enantio-selective manner. One of the products is converted to a heavily functionalized tetracyclic indolinone derivative The experimental part of the paper was very detailed, including the reaction process of 4-Chloro-2-iodoaniline(cas: 63069-48-7Recommanded Product: 4-Chloro-2-iodoaniline)

4-Chloro-2-iodoaniline(cas: 63069-48-7) belongs to anime. In organic chemistry, amines are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (NH3), wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group (these may respectively be called alkylamines and arylamines; amines in which both types of substituent are attached to one nitrogen atom may be called alkylarylamines).Recommanded Product: 4-Chloro-2-iodoaniline

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

《Gold Catalyzed Decarboxylative Cross-Coupling of Iodoarenes》 was written by Daley, Ryan A.; Morrenzin, Aaron S.; Neufeldt, Sharon R.; Topczewski, Joseph J.. Reference of 1-Iodonaphthalene And the article was included in Journal of the American Chemical Society in 2020. The article conveys some information:

Decarboxylative cross-coupling of (hetero)aryl carboxylates with iodoarenes in the presence of a gold cata-lyst (>25 examples, up to 96% yield) was reported. This reaction was site specific, which overcomes prior limitations associated with gold cat-alyzed oxidative coupling reactions. The reactivity of the (hetero)aryl carboxylate correlated qual. to the field effect pa-rameter (Fortho). Reactions with isolated gold complexes and DFT calculations supported a mechanism proceeding through oxida-tive addition at a gold(I) cation with decarboxylation being viable at either gold(I) or silver(I) species.1-Iodonaphthalene(cas: 90-14-2Reference of 1-Iodonaphthalene) was used in this study.

1-Iodonaphthalene(cas: 90-14-2) 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.Reference of 1-Iodonaphthalene

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

《Synthesis of Acyclic Aliphatic Amides with Contiguous Stereogenic Centers via Palladium-Catalyzed Enantio-, Chemo- and Diastereoselective Methylene C(sp3)-H arylation》 was written by Han, Ye-Qiang; Yang, Xu; Kong, Ke-Xin; Deng, Yao-Ting; Wu, Le-Song; Ding, Yi; Shi, Bing-Feng. Category: iodides-buliding-blocks And the article was included in Angewandte Chemie, International Edition in 2020. The article conveys some information:

The enantioselective desymmetrizing C-H activation of α-gem-dialkyl acyclic amides remains challenging because the availability of four chem. identical unbiased methylene C(sp3)-H bonds and increased rotational freedoms of the acyclic systems add tremendous difficulties for chemo- and stereocontrol. We have developed a method for the synthesis of acyclic aliphatic amides with α,β-contiguous stereogenic centers via PdII-catalyzed asym. arylation of unbiased methylene C(sp3)-H, in good yields and with high levels of enantio-, chemo- and diastereoselectivity [up to >99% ee and >20:1 d.r.; e.g., amide I + PhI → II (75%, > 20:1 d.r., 98% ee)]. Successive application of this method enables the sequential arylation of the gem-dialkyl groups with two different aryl iodides, giving a range of β-Ar1-β’-Ar2-aliphatic acyclic amides containing three contiguous stereogenic centers with excellent diastereoselectivity. In the experiment, the researchers used many compounds, for example, 3-Iodophenol(cas: 626-02-8Category: iodides-buliding-blocks)

3-Iodophenol(cas: 626-02-8) belongs to organic iodides. The carbon-iodine bond is weaker than other carbon-halogen bonds due to the poor electronegative nature of the iodine atom. Category: iodides-buliding-blocks Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.

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

《Excimer formation of aryl iodides chemisorbed on gold nanoparticles for the significant enhancement of photoluminescence》 was published in Journal of Physical Chemistry Letters in 2020. These research results belong to Maity, Prasenjit; Sasai, Kenji; Dhital, Raghu Nath; Sakai, Hayato; Hasobe, Taku; Sakurai, Hidehiro. Quality Control of 4-Iodobenzoic acid The article mentions the following:

The photoluminescence properties of aryl iodides chemisorbed on gold nanoparticles were examined Chemisorption of a series of aryl iodides onto poly(N-vinylpyrrolidone)-protected Au nanoparticles (Au:PVP) in solution resulted in highly enhanced luminescence. Kinetic studies revealed that the photoluminescence is derived from the excimer formation of aryl iodides on Au:PVP, and the process is significantly faster than intersystem crossing by the heavy atom. After reading the article, we found that the author used 4-Iodobenzoic acid(cas: 619-58-9Quality Control of 4-Iodobenzoic acid)

4-Iodobenzoic acid(cas: 619-58-9) belongs to organic iodides. The carbon-iodine bond is weaker than other carbon-halogen bonds due to the poor electronegative nature of the iodine atom. Quality Control of 4-Iodobenzoic acid Organic iodides can be alkyl, alkenyl, or alkynyl, and all of them are very reactive toward with many kinds of nucleophiles.

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

《Regioselective Monohalogenation and Homo/Hetero Dihalogenation of Benzothioxanthene Monoimide》 was published in European Journal of Organic Chemistry in 2020. These research results belong to Dalinot, Clement; Simon Marques, Pablo; Andres Castan, Jose M.; Josse, Pierre; Allain, Magali; Abad Galan, Laura; Monnereau, Cyrille; Maury, Olivier; Blanchard, Philippe; Cabanetos, Clement. Name: 1-Iodopyrrolidine-2,5-dione The article mentions the following:

Through the preparation and characterization of five new derivatives, the regioselective mono and di, homo and hetero, halogenation of the benzothioxanthene (BTXI) core is demonstrated herein. All structurally solved by X-ray crystallog., these complementary functionalized building blocks open doors to the design of new sym. and asym. π-conjugated systems based on this promising but still under-explored rylene. In the experimental materials used by the author, we found 1-Iodopyrrolidine-2,5-dione(cas: 516-12-1Name: 1-Iodopyrrolidine-2,5-dione)

1-Iodopyrrolidine-2,5-dione(cas: 516-12-1) is used in the preparation of vinyl sulfones from olefins and benzenesulfinic acid. It acts as a source for I+ and involved in Hunsdiecker reactions for the conversion of cinnamic acids, and propiolic acids to the corresponding alfa-halostyrenes and 1-halo-1-alkynes respectively. Name: 1-Iodopyrrolidine-2,5-dione

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

《Intermolecular Alkene Difunctionalization via Gold-Catalyzed Oxyarylation》 was published in Angewandte Chemie, International Edition in 2020. These research results belong to Zhang, Shuyao; Wang, Chenhuan; Ye, Xiaohan; Shi, Xiaodong. Quality Control of 1-Iodo-4-methylbenzene The article mentions the following:

The gold-catalyzed intermol. oxyarylation of alkenes is reported. This work employed the oxidative addition of aryl iodides to Me-DalphosAu+ for the formation of a AuIII-Ar intermediate. The better binding ability of alkenes over O nucleophiles ensured the success of intermol. oxyarylation, giving desired products with a broad substrate scope and high efficiency (>50 examples with up to 95% yield). One-pot converting of methoxy groups into other nucleophiles allowed achieving alkene difunctionalization with the construction of C-N, C-S, and C-C bonds under mild conditions. In the experimental materials used by the author, we found 1-Iodo-4-methylbenzene(cas: 624-31-7Quality Control of 1-Iodo-4-methylbenzene)

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.Quality Control of 1-Iodo-4-methylbenzene

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

《Nickel/Photoredox-Catalyzed Asymmetric Reductive Cross-Coupling of Racemic α-Chloro Esters with Aryl Iodides》 was published in Angewandte Chemie, International Edition in 2020. These research results belong to Guan, Haixing; Zhang, Qianwen; Walsh, Patrick J.; Mao, Jianyou. Recommanded Product: 1-Iodo-4-methylbenzene The article mentions the following:

A unique nickel/organic photoredox co-catalyzed asym. reductive cross-coupling between α-chloro esters and aryl iodides is developed. This cross-electrophile coupling reaction employs an organic reductant (Hantzsch ester), whereas most reductive cross-coupling reactions use stoichiometric metals. A diverse array of valuable α-aryl esters is formed under these conditions with high enantioselectivities (up to 94%) and good yields (up to 88%). α-Aryl esters represent an important family of nonsteroidal anti-inflammatory drugs. This novel synergistic strategy expands the scope of Ni-catalyzed reductive asym. cross-coupling reactions. In the experiment, the researchers used 1-Iodo-4-methylbenzene(cas: 624-31-7Recommanded Product: 1-Iodo-4-methylbenzene)

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.Recommanded Product: 1-Iodo-4-methylbenzene

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

The author of 《Palladium-catalyzed regioselective C2-arylation of 5-aminoindole》 were Taskesenligil, Yunus; Lafzi, Ferruh; Kilic, Haydar; Saracoglu, Nurullah. And the article was published in Journal of Heterocyclic Chemistry in 2019. Synthetic Route of C6H4BrI The author mentioned the following in the article:

Pd(II)-catalyzed C-H arylations of 5-aminoindole using iodobenzenes as aryl source was studied. Despite pivalamide directing group at 5-position of the indole, the direct C2-arylation of the indole observed in high yields and with high regioselectivity.1-Bromo-4-iodobenzene(cas: 589-87-7Synthetic Route of C6H4BrI) was used in this study.

1-Bromo-4-iodobenzene(cas: 589-87-7) is mainly used as the OLED pharmaceutical intermediate, as reagent for in situ desilylation and coupling of silylated alkynes, as substrate in copper-free Sonogashira coupling in aqueous acetone..Synthetic Route of C6H4BrI It is also used in synthesis of β,β,dibromostyrenes, as starting reagent in the total syntheses of ent-conduramine A and ent-7-deoxypancratistatin (alkaloids)

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

The author of 《Iridium-Catalyzed Silylation of C-H Bonds in Unactivated Arenes: A Sterically Encumbered Phenanthroline Ligand Accelerates Catalysis》 were Karmel, Caleb; Chen, Zhewei; Hartwig, John F.. And the article was published in Journal of the American Chemical Society in 2019. Quality Control of 1-Chloro-3-iodobenzene The author mentioned the following in the article:

We report a new system for the silylation of aryl C-H bonds. The combination of [Ir(cod)(OMe)]2 and 2,9-Me2-phenanthroline (2,9-Me2-phen) catalyzes the silylation of arenes at lower temperatures and with faster rates than those reported previously, when the hydrogen byproduct is removed, and with high functional group tolerance and regioselectivity. Inhibition of reactions by the H2 byproduct is shown to limit the silylation of aryl C-H bonds in the presence of the most active catalysts, thereby masking their high activity. Anal. of initial rates uncovered the high reactivity of the catalyst containing the sterically hindered 2,9-Me2-phen ligand but accompanying rapid inhibition by hydrogen. With this catalyst, under a flow of nitrogen to remove hydrogen, electron-rich arenes, including those containing sensitive functional groups, undergo silylation in high yield for the first time, and arenes that underwent silylation with prior catalysts react over much shorter times with lower catalyst loadings. The synthetic value of this methodol. is demonstrated by the preparation of key intermediates in the synthesis of medicinally important compounds in concise sequences comprising silylation and functionalization. Mechanistic studies demonstrate that the cleavage of the aryl C-H bond is reversible and that the higher rates observed with the 2,9-Me2-phen ligand are due to a more thermodynamically favorable oxidative addition of aryl C-H bonds. In the experimental materials used by the author, we found 1-Chloro-3-iodobenzene(cas: 625-99-0Quality Control of 1-Chloro-3-iodobenzene)

1-Chloro-3-iodobenzene(cas: 625-99-0) belongs to organic iodides. Generally organic iodides can be divided into two classes of alkyl iodides and aryl iodides. Quality Control of 1-Chloro-3-iodobenzene Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics.

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

The author of 《Ligand-Enabled PdII-Catalyzed Iterative γ-C(sp3)-H Arylation of Free Aliphatic Acid》 were Dolui, Pravas; Das, Jayabrata; Chandrashekar, Hediyala B.; Anjana, S. S.; Maiti, Debabrata. And the article was published in Angewandte Chemie, International Edition in 2019. Recommanded Product: 1-Iodo-4-methylbenzene The author mentioned the following in the article:

C-H functionalization of aliphatic carboxylic acids without attaching exogenous auxiliary has been so far limited at the proximal β-position. In this work, we demonstrate a ligand enabled palladium catalyzed first regioselective distal γ-C(sp3)-H functionalization of aliphatic carboxylic acids without incorporating an exogenous directing group. Aryl iodides containing versatile functional groups including complex organic mols. are well tolerated with good to excellent yields during the γ-C(sp3)-H arylation reaction. Interestingly, weak coordination of carboxylate group can be further extended for sequential hetero di-arylation. Application of the protocol has been showcased by synthesizing substituted α-tetralone. Mechanistic investigations have been carried out to shed light on the reaction pathway. In the part of experimental materials, we found many familiar compounds, such as 1-Iodo-4-methylbenzene(cas: 624-31-7Recommanded Product: 1-Iodo-4-methylbenzene)

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.Recommanded Product: 1-Iodo-4-methylbenzene

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