Category: iodides-buliding-blocks

A Convenient Synthesis of 2-Arylbenzo[b]furans from Aryl Halides and 2-Halophenols by Catalytic One-Pot Cascade Method was written by Bosiak, Mariusz Jan. And the article was included in ACS Catalysis in 2016.COA of Formula: C6H4BrIO This article mentions the following:

The development of a multicatalytic one-pot synthesis of 2-arylbenzofurans starting from aryl halides and 2-halophenols is described. The protocol involves two Sonogashira coupling reactions, followed by 2-ethynylphenol cyclization leading to 2-arylbenzofuran derivatives The process occurs smoothly under mild conditions, giving products in good yields, and can be applied to many 2-arylbenzofurans substituted both at 2-aryl position and in the benzodifuran moiety. Substituents such as halogens, hydroxyl, cyano, nitro, and amino groups are tolerated, enabling further functionalization of the system. In the experiment, the researchers used many compounds, for example, 4-Bromo-2-iodophenol (cas: 207115-22-8COA of Formula: C6H4BrIO).

4-Bromo-2-iodophenol (cas: 207115-22-8) belongs to iodide derivatives. Organic iodides are organic compounds containing a carbon-iodine (C-I) bond. The carbon-iodine bond is weaker than other carbon-halogen bonds due to the poor electronegative nature of the iodine atom. The C–I bond is the weakest of the carbon–halogen bonds. These bond strengths correlate with the electronegativity of the halogen, decreasing in the order F > Cl > Br > I.COA of Formula: C6H4BrIO

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

Synthesis, configuration judgment and potentiation activity of (2S,3S,E)-4-(3,4- dihydroxybenzylidene)-3-(3,4-dihydroxyphenyl)- 5-oxotetrahydrofuran-2-carboxylic acid was written by Zhang, Jun-Liang;Lv, Zhi-Liang;Zhong, Jia-Liang;Chen, Dai-Jie;Li, Mo-Ying;Zhang, Jian-Bin. And the article was included in Chinese Journal of Structural Chemistry in 2017.Formula: C8H9IO2 This article mentions the following:

The title compound (2S,3S,E)-4-(3,4-dihydroxybenzylidene)-3-(3,4-dihydroxyphenyl)- 5-oxotetrahydrofuran-2-carboxylic acid was synthesized and the 2D structure was characterized by 1H-NMR 13C-NMR and LCMS. The absolute configuration was determined by single-crystal X-ray diffraction of the key intermediate (2S,3S,E)-Et 4-(3,4-dimethoxybenzylidene)- 3-(3,4-dimethoxyphenyl)-5-oxotetrahydrofuran-2-carboxylate. The crystal belongs to tetragonal system, space group P41 with a = 13.0665(2), b = 13.0665(2), c = 13.4735(2) Å, V = 2300.4(6) Å3, Z = 4, Dc = 1.278 g/cm3, μ(CuKa) = 0.801 mm-1, F(000) = 936, S = 1.050, R = 0.0364 and wR (I > 2s(I)) = 0.1071. X-ray diffraction results showed that the mol. structure is stabilized totally by Van der Waals force. The antibacterial activity tests showed that the title compound possesses slight synergistic effect against MRSA and Acinetobacter baumanii. In the experiment, the researchers used many compounds, for example, 4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2Formula: C8H9IO2).

4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2) belongs to iodide derivatives. Organoiodine compounds occur widely in organic chemistry, but are relatively rare in nature. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.Formula: C8H9IO2

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

Carbo-Carboxylation of Alkenes via Intramolecular Heck Carbonylation Utilizing CO₂ and Hydrosilane was written by Wang, Meng-Meng;Lu, Sheng-Mei;Li, Can. And the article was included in ACS Catalysis in 2022.Quality Control of 4-Bromo-2-iodophenol This article mentions the following:

Starting from diverse alkene-tethered aryl halides 2-X-3-R-4-R¹-5-R²C₆HYZ(CH₂)_nC(=CH₂)R³ [R = H, OMe, Cl; R¹ = H, Me, t-Bu, Br, F, Cl; R² = H, OMe, Cl, COOMe; R³ = Me, n-Bu, methoxymethyl; X = Br, I; Y = Z = O, CH₂; n = 0, 1] and silyl formate formed in situ from CO₂ and PMHS (polymethylhydrosiloxane), the carbo-carboxylation of alkenes has been achieved using an easily accessible Pd/monophosphine ligand combination as the catalyst. This protocol provides competent access to construct a series of 2,3-dihydrobenzofurans, chromans, isochroman, indanes and tetralins bearing a β-acid moiety I in moderate to excellent yield. Addnl., the example of domino carbo-carbonylation reactions has been demonstrated using diene-tethered aryl iodide as starting material, forming oxygen-containing bicyclic products I in good yield. It is speculated that the carbo-carboxylation reaction of alkenes proceeds via a carbo-silyloxycarbonylation pathway. In the experiment, the researchers used many compounds, for example, 4-Bromo-2-iodophenol (cas: 207115-22-8Quality Control of 4-Bromo-2-iodophenol).

4-Bromo-2-iodophenol (cas: 207115-22-8) belongs to iodide derivatives. Organic iodides are widely used in organic synthesis. Halogenation of aromatic hydrocarbons is a very important reaction via an electrophilic aromatic substitution. 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.Quality Control of 4-Bromo-2-iodophenol

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

The Catalyst-Controlled Regiodivergent Chlorination of Phenols was written by Maddox, Sean M.;Dinh, Andrew N.;Armenta, Felipe;Um, Joann;Gustafson, Jeffrey L.. And the article was included in Organic Letters in 2016.Product Details of 289039-26-5 This article mentions the following:

Different catalysts are demonstrated to overcome or augment a substrate’s innate regioselectivity. Nagasawa’s bis-thiourea catalyst was found to overcome the innate para-selectivity of electrophilic phenol chlorination, yielding ortho-chlorinated phenols that are not readily obtainable via canonical electrophilic chlorinations. Conversely, a phosphine sulfide derived from 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) was found to enhance the innate para-preference of phenol chlorination. In the experiment, the researchers used many compounds, for example, 2-Chloro-5-iodophenol (cas: 289039-26-5Product Details of 289039-26-5).

2-Chloro-5-iodophenol (cas: 289039-26-5) belongs to iodide derivatives. Iodide-containing intermediates are common in organic synthesis, because of the easy formation and cleavage of the C–I bond. 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.Product Details of 289039-26-5

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

Design and Synthesis of Pyrrolo[2,3-d]pyrimidine-Derived Leucine-Rich Repeat Kinase 2 (LRRK2) Inhibitors Using a Checkpoint Kinase 1 (CHK1)-Derived Crystallographic Surrogate was written by Williamson, Douglas S.;Smith, Garrick P.;Mikkelsen, Gitte K.;Jensen, Thomas;Acheson-Dossang, Pamela;Badolo, Lassina;Bedford, Simon T.;Chell, Victoria;Chen, I-Jen;Dokurno, Pawel;Hentzer, Morten;Newland, Samantha;Ray, Stuart C.;Shaw, Terry;Surgenor, Allan E.;Terry, Lindsey;Wang, Yikang;Christensen, Kenneth V.. And the article was included in Journal of Medicinal Chemistry in 2021.Electric Literature of C6H2Cl2IN3 This article mentions the following:

Inhibitors of leucine-rich repeat kinase 2 (LRRK2) and mutants, such as G2019S, have potential utility in Parkinson’s disease treatment. Fragment hit-derived pyrrolo[2,3-d]pyrimidines underwent optimization using X-ray structures of LRRK2 kinase domain surrogates, based on checkpoint kinase 1 (CHK1) and a CHK1 10-point mutant. (2R)-2-Methylpyrrolidin-1-yl derivative I (LRRK2 G2019S cK_i 0.7 nM, LE 0.66) was identified, with increased potency consistent with an X-ray structure of 18/CHK1 10-pt. mutant showing the 2-Me substituent proximal to Ala147 (Ala2016 in LRRK2). Further structure-guided elaboration of I gave the 2-[(1,3-dimethyl-1H-pyrazol-4-yl)amino] deriv II. Optimization of II afforded diastereomeric oxolan-3-yl derivatives III and IV, which demonstrated a favorable in vitro PK profile, although they displayed species disconnects in the in vivo PK profile, and a propensity for P-gp- and/or BCRP-mediated efflux in a mouse model. Compounds III and IV demonstrated high potency and exquisite selectivity for LRRK2 and utility as chem. probes for the study of LRRK2 inhibition. In the experiment, the researchers used many compounds, for example, 2,4-Dichloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (cas: 1012785-51-1Electric Literature of C6H2Cl2IN3).

2,4-Dichloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (cas: 1012785-51-1) belongs to iodide derivatives. Organic iodides are widely used in organic synthesis. Halogenation of aromatic hydrocarbons is a very important reaction via an electrophilic aromatic substitution. 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.Electric Literature of C6H2Cl2IN3

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

Palladium-catalyzed triple coupling of 2-iodoanisoles with aryl iodides to access 6H-dibenzopyrans was written by Chen, Li-Ping;Cheng, Shu-Lin;Fan, Xin-Yue;Zhu, Ji-Fa;Wang, Bi-Qin;Feng, Chun;Xiang, Shi-Kai. And the article was included in Organic Chemistry Frontiers in 2022.Quality Control of 3-Iodo-4-methoxybenzaldehyde This article mentions the following:

A palladium-catalyzed triple coupling of 2-iodoanisoles with aryl iodides was developed. 3-Methyl-2-pyridone was used as a ligand to accelerate the cross-coupling and suppress the homo-coupling of 2-iodoanisoles. A variety of 6H-dibenzopyran derivatives such as I [R = H, F, Cl, etc., R¹ = 4-Me, 4-F, 4-MeO, etc.; R² = 8-Me, 8-Cl, 8-Ph, etc.] was prepared by this method. In the experiment, the researchers used many compounds, for example, 3-Iodo-4-methoxybenzaldehyde (cas: 2314-37-6Quality Control of 3-Iodo-4-methoxybenzaldehyde).

3-Iodo-4-methoxybenzaldehyde (cas: 2314-37-6) belongs to iodide derivatives. Organic iodides can be alkyl, alkenyl, or alkynyl, and all of them are very reactive toward with many kinds of nucleophiles. The C–I bond is the weakest of the carbon–halogen bonds. These bond strengths correlate with the electronegativity of the halogen, decreasing in the order F > Cl > Br > I.Quality Control of 3-Iodo-4-methoxybenzaldehyde

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

NiH-catalyzed reductive hydrocarbonation of enol esters and ethers was written by Wang, Xiao-Xu;Yu, Lu;Lu, Xi;Zhang, Zhi-Lin;Liu, De-Guang;Tian, Changlin;Fu, Yao. And the article was included in CCS Chemistry in 2022.COA of Formula: C4H8ClI This article mentions the following:

Chiral dialkyl carbinols and their derivatives are significant synthetic building blocks in organic chem. and related fields. The development of convenient and efficient methods to access these compounds has long been an important endeavor. Herein, authors report a NiH-catalyzed reductive hydroalkylation and hydroarylation of enol esters and ethers. α-Oxoalkyl organonickel species were generated in situ in a catalytic mode and then participated in cross-coupling with alkyl or aryl halides. This approach enabled C(sp3)-C(sp3) and C(sp3)-C(sp2) bond formation under mild reductive conditions with simple operations, thereby boosting a broad substrate scope and good functional compatibility. Esters of enantioenriched dialkyl carbinols were accessed in a catalytic asym. version. Mechanistic studies demonstrated that this reaction proceeded through a syn-addition of Ni-H intermediate to an enol ester with high regio- and enantioselectivity. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9COA of Formula: C4H8ClI).

1-Chloro-4-iodobutane (cas: 10297-05-9) belongs to iodide derivatives. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine. 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.COA of Formula: C4H8ClI

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

Divergent Synthesis of Fused Tetracyclic Heterocycles from Diarylalkynes Enabled by the Selective Insertion of Isocyanide was written by Li, Meng;Zhang, Ruixue;Gao, Qiushan;Jiang, Huanfeng;Lei, Ming;Wu, Wanqing. And the article was included in Angewandte Chemie, International Edition in 2022.Name: 4-Bromo-2-iodophenol This article mentions the following:

Herein, a direct and efficient synthesis of diverse polysubstituted fused tetracyclic heterocycles with good functional group tolerance from diarylalkynes under different palladium catalytic systems was presented. In this chem., an unprecedented intermol. nucleopalladation of diarylalkynes through the highly selective sequential double insertion of isocyanide was achieved for the first time. The practicality of this method was further demonstrated by the construction of various bioactive mols. and important structural motifs, with potential applications in materials science and biochem. In addition, d. functional theory calculations (DFT) elucidated an interesting “Pd walk” during the cyclization process. In the experiment, the researchers used many compounds, for example, 4-Bromo-2-iodophenol (cas: 207115-22-8Name: 4-Bromo-2-iodophenol).

4-Bromo-2-iodophenol (cas: 207115-22-8) belongs to iodide derivatives. Iodide-containing intermediates are common in organic synthesis, because of the easy formation and cleavage of the C–I bond. Organoiodine lubricants can be used with titanium, stainless steels, and other metals which tend to seize up with conventional lubricants: organoiodine lubricants can be used in turbines and spacecraft, and as a cutting oil in machining.Name: 4-Bromo-2-iodophenol

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

Stereocontrolled Synthesis of Fluorinated Isochromans via Iodine(I)/Iodine(III) Catalysis was written by Hafliger, Joel;Sokolova, Olga O.;Lenz, Madina;Daniliuc, Constantin G.;Gilmour, Ryan. And the article was included in Angewandte Chemie, International Edition in 2022.Category: iodides-buliding-blocks This article mentions the following:

The ubiquity of isochromans across the bioactive small mol. spectrum, the prominence of the anomeric effect in regulating conformation and the metabolic lability of the benzylic position, iodine(I)/iodine(III) catalysis was leveraged for the stereocontrolled generation of selectively fluorinated analogs. To augment the current arsenal of fluorocyclization reactions involving carboxylic acid derivatives, the reaction of readily accessible 2-vinyl benzaldehydes was disclosed (up to >95 : 05 d.r. and 97 : 03 e.r.). Key stereoelectronic interactions manifest themselves in the X-ray crystal structures of the products, thereby validating the [CH₂-CHF] fragment as a stereoelectronic mimic of the [O-CH(OR)] acetal motif. In the experiment, the researchers used many compounds, for example, Methyl 3,5-dihydroxy-4-iodobenzoate (cas: 338454-02-7Category: iodides-buliding-blocks).

Methyl 3,5-dihydroxy-4-iodobenzoate (cas: 338454-02-7) belongs to iodide derivatives. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine. Polyiodoorganic compounds are sometimes employed as X-ray contrast agents, in fluoroscopy, a type of medical imaging. This application exploits the X-ray absorbing ability of the heavy iodine nucleus.Category: iodides-buliding-blocks

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

Palladium-Catalyzed Enantioselective Cyclization of 1,6-Enynes through Intramolecular Chlorine Transfer as a Novel Strategy for Asymmetric Halopalladation was written by Tang, Junlong;Zhang, Liren;Wu, Wanqing;Yang, Shaorong;Jiang, Huanfeng. And the article was included in Chemistry – A European Journal.Electric Literature of C8H5IS This article mentions the following:

Herein, an intramol. chlorine transfer strategy is used to accomplish the enantioselective chloropalladation cyclization of 1,6-enynes RCCC(O)OCH₂CH=CHCH₂Cl (R = Et, Ph, thiophen-3-yl, 1-benzothiophen-3-yl, etc.). This reaction provides a redox-neutral approach to a variety of chiral α-chloromethylene-γ-butyrolactones I with excellent E selectivity and enantioselectivity. The precisely controlled coordination of palladium with both the in situ generated nucleophilic species and the monodentate phosphoramidite ligand is crucial for enantioselectivity. In the experiment, the researchers used many compounds, for example, 3-Iodobenzo[b]thiophene (cas: 36748-88-6Electric Literature of C8H5IS).

3-Iodobenzo[b]thiophene (cas: 36748-88-6) belongs to iodide derivatives. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine. The C–I bond is the weakest of the carbon–halogen bonds. These bond strengths correlate with the electronegativity of the halogen, decreasing in the order F > Cl > Br > I.Electric Literature of C8H5IS

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