Category: iodides-buliding-blocks

Fanourakis, Alexander; Williams, Benjamin D.; Paterson, Kieran J.; Phipps, Robert J. published an article in 2021. The article was titled 《Enantioselective Intermolecular C-H Amination Directed by a Chiral Cation》, and you may find the article in Journal of the American Chemical Society.Formula: C6H5IO The information in the text is summarized as follows:

A family of anionic variants of the best-in-class catalyst for Rh-catalyzed C-H amination, Rh2(esp)2, with which the chiral cations are associated And derived from quaternized cinchona alkaloids, has been described. These ion-paired catalysts enable high levels of enantioselectivity to be achieved in the benzylic C-H amination of substrates R(CH2)4OH (R = Ph, 1-naphthyl, 3-methylthiophen-2-yl, etc.) bearing pentyl hydroxyl groups. Addnl., the quinoline of the chiral cation appears to engage in axial ligation to the rhodium complex, providing improved yields of products RCH(NHS(O)2OCH2R1)(CH2)3OH (R1 = (CF2)2CF3) vs. Rh2(esp)2 and highlighting the dual role that the cation is playing. These results underline the potential of using chiral cations to control enantioselectivity in challenging transition-metal-catalyzed transformations. In addition to this study using 3-Iodophenol, there are many other studies that have used 3-Iodophenol(cas: 626-02-8Formula: C6H5IO) was used in this study.

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. Formula: C6H5IO 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

《Visible-light-induced triple catalysis for a ring-opening cyanation of cyclopropyl ketones》 was published in Chemical Communications (Cambridge, United Kingdom) in 2020. These research results belong to Liu, Jing; Liu, Xiao-Peng; Wu, Hong; Wei, Yi; Lu, Fu-Dong; Guo, Kai-Rui; Cheng, Ying; Xiao, Wen-Jing. Recommanded Product: Trimethylsulfoxonium iodide The article mentions the following:

An unprecedented triple catalytic, general ring-opening cyanation reaction of cyclopropyl ketones I (R = Ph, 3,4-dichlorophenyl, prop-1-en-1-yl, etc.; R1 = H, CO2C(CH3)3; R2 = Ph, 4-fluorophenyl, 2-naphthyl, etc.) for the construction of γ-cyanoketones R2C(O)CH2CH(R1)CH(R)CN is described. The key is to merge photoredox catalysis with Lewis acid catalysis and copper catalysis to enable the selective cleavage of the carbon-carbon bonds and the selective coupling of the generated radical and cyanide anion. In the experimental materials used by the author, we found Trimethylsulfoxonium iodide(cas: 1774-47-6Recommanded Product: Trimethylsulfoxonium iodide)

Trimethylsulfoxonium iodide(cas: 1774-47-6) is a sulfoxonium salt. It is used to generate dimethyloxosulfonium methylide by reaction with sodium hydride. The latter compound is used as a methylene-transfer reagent, and is used to prepare epoxides.Recommanded Product: Trimethylsulfoxonium iodide

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

The author of 《Carboxylate-Assisted Oxidative Addition to Aminoalkyl PdII Complexes: C(sp3)-H Arylation of Alkylamines by Distinct PdII/PdIV Pathway》 were Whitehurst, William G.; Blackwell, J. Henry; Hermann, Gary N.; Gaunt, Matthew J.. And the article was published in Angewandte Chemie, International Edition in 2019. Name: 2-Iodobenzoic acid The author mentioned the following in the article:

Reported is the discovery of an approach to functionalize secondary alkylamines using 2-halobenzoic acids as aryl-transfer reagents. These reagents promote an unusually mild carboxylate-assisted oxidative addition to alkylamine-derived palladacycles. In the presence of AgI salts, a decarboxylative C(sp3)-C(sp2) bond reductive elimination leads to γ-aryl secondary alkylamines and renders the carboxylate motif a traceless directing group. Stoichiometric mechanistic studies were effectively translated to a Pd-catalyzed γ-C(sp3)-H arylation process for secondary alkylamines. In the experiment, the researchers used 2-Iodobenzoic acid(cas: 88-67-5Name: 2-Iodobenzoic acid)

2-Iodobenzoic acid(cas: 88-67-5) 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. Name: 2-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

The author of 《Semi-heterogeneous Dual Nickel/Photocatalysis using Carbon Nitrides: Esterification of Carboxylic Acids with Aryl Halides》 were Pieber, Bartholomaeus; Malik, Jamal A.; Cavedon, Cristian; Gisbertz, Sebastian; Savateev, Aleksandr; Cruz, Daniel; Heil, Tobias; Zhang, Guigang; Seeberger, Peter H.. And the article was published in Angewandte Chemie, International Edition in 2019. Quality Control of 1-Iodo-4-methylbenzene The author mentioned the following in the article:

Cross-coupling reactions mediated by dual nickel/photocatalysis are synthetically attractive but rely mainly on expensive, non-recyclable noble-metal complexes as photocatalysts. Heterogeneous semiconductors, which are commonly used for artificial photosynthesis and wastewater treatment, are a sustainable alternative. Graphitic carbon nitrides, a class of metal-free polymers that can be easily prepared from bulk chems., are heterogeneous semiconductors with high potential for photocatalytic organic transformations. Here, we demonstrate that graphitic carbon nitrides in combination with nickel catalysis can induce selective C-O cross-couplings of carboxylic acids with aryl halides, yielding the resp. aryl esters in excellent yield and selectivity. The heterogeneous organic photocatalyst exhibits a broad substrate scope, is able to harvest green light, and can be recycled multiple times. In situ FTIR was used to track the reaction progress to study this transformation at different irradiation wavelengths and reaction scales. 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

In 2016,Castello-Mico, Alicia; Herbert, Simon A.; Leon, Thierry; Bein, Thomas; Knochel, Paul published 《Functionalizations of Mixtures of Regioisomeric Aryllithium Compounds by Selective Trapping with Dichlorozirconocene》.Angewandte Chemie, International Edition published the findings.Recommanded Product: 624-73-7 The information in the text is summarized as follows:

The reaction of mixtures of aryllithium regioisomers obtained either by directed lithiation or by Br/Li exchange with substoichiometric amounts of Cp2ZrCl2 proceeds with high regioselectivity. The least sterically hindered regioisomeric aryllithium is selectively transmetalated to the corresponding arylzirconium species leaving the more hindered aryllithium ready for various reactions with electrophiles. As an application, these regioselective transmetalations from Li to Zr were used to prepare all three lithiated regioisomers of 1,3-bis(trifluoromethyl)benzene. In the experiment, the researchers used many compounds, for example, 1,2-Diiodoethane(cas: 624-73-7Recommanded Product: 624-73-7)

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.Recommanded Product: 624-73-7

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

Application of 589-87-7In 2020 ,《Transition metal-free coupling reactions of benzylic trimethylammonium salts with di(hetero)aryl disulfides and diselenides》 was published in Chemical Communications (Cambridge, United Kingdom). The article was written by Li, Fuhai; Wang, Dan; Chen, Hongyi; He, Ze; Zhou, Lihong; Zeng, Qingle. The article contains the following contents:

A new protocol was developed to synthesize (enantioenriched) thioethers ArCH2SAr1 [Ar = 2-thienyl, Ph, 4-FC6H4, etc.; Ar1 = Ph, 2-pyridyl, 4-O2NC6H4, etc.; stereo = rac, R, S] and selenoethers Ar2CH2SeAr3 [Ar2 = 2-pyridyl, 4-F3CC6H4, 1-naphthyl, etc.; Ar3 = 2-thienyl, Ph, 4-NCC6H4, etc.; stereo = rac, R, S] from (chiral) benzylic trimethylammonium salts and di(hetero)aryl disulfides or diselenides. These synthesis were promoted by presence of weak base and did not require the use of any transition metal, and resulted in target products with good to excellent yields (72-94%). Using quaternary ammonium salts synthesized from enantiomerically enriched amines led to highly enantiopure benzylic thioethers and selenoethers (94-99% ee) with configurations reversed from those of their enantioenriched quaternary ammonium salts. In the experiment, the researchers used 1-Bromo-4-iodobenzene(cas: 589-87-7Application of 589-87-7)

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..Application of 589-87-7 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