Category: iodides-buliding-blocks

One-Pot Direct Synthesis of Weinreb Amides From Aryl and Hetero Aryl Halides Using Co₂(CO)₈ as an Effective CO Source Under Conventional Thermal Heating was written by Baburajan, Poongavanam;Elango, Kuppanagounder P.. And the article was included in Synthetic Communications in 2015.Category: iodides-buliding-blocks This article mentions the following:

A successful protocol for the synthesis of Weinreb amides directly from aryl halides via aminocarbonylation with N,O-dimethylhydroxylamine using Co₂(CO)₈ as an in situ CO source has been demonstrated. The effects of various reaction parameters such as temperature, base, and CO source have also been investigated and optimized. In the experiment, the researchers used many compounds, for example, 4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2Category: iodides-buliding-blocks).

4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2) belongs to iodide derivatives. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation 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.Category: iodides-buliding-blocks

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

Rh-Catalyzed General Method for Directed C-H Functionalization via Decarbonylation of in-Situ-Generated Acid Fluorides from Carboxylic Acids was written by He, Bangyue;Liu, Xiaojie;Li, Hongyi;Zhang, Xiaofeng;Ren, Yuxi;Su, Weiping. And the article was included in Organic Letters in 2021.COA of Formula: C8H7IO2 This article mentions the following:

A Rh-catalyzed decarbonylative C-H coupling of in-situ-generated acid fluorides with amide substrates bearing ortho-Csp²-H bonds has been developed. This method enables alkyl, aryl, and alkenyl carboxylic acids to undergo decarbonylative coupling with C-H bonds of (hetero)aromatic or alkenyl amides in generally good yields via the in situ conversion of carboxylic acids into acid fluorides and also allows for the functionalization of a series of structurally complex carboxyl-containing natural products and pharmaceuticals as well as pharmaceutical amide derivatives In the experiment, the researchers used many compounds, for example, 3-Iodo-2-methylbenzoic acid (cas: 133232-56-1COA of Formula: C8H7IO2).

3-Iodo-2-methylbenzoic acid (cas: 133232-56-1) belongs to iodide derivatives. Generally organic iodides can be divided into two classes of alkyl iodides and aryl iodides. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. 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. This periodic order also follows the atomic radius of halogens and the length of the carbon-halogen bond.COA of Formula: C8H7IO2

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

Rapid Access to Azabicyclo[3.3.1]nonanes by a Tandem Diverted Tsuji-Trost Process was written by Steeds, Hannah G.;Knowles, Jonathan P.;Yu, Wai L.;Richardson, Jeffery;Cooper, Katie G.;Booker-Milburn, Kevin I.. And the article was included in Chemistry – A European Journal in 2020.SDS of cas: 877264-43-2 This article mentions the following:

A three-step synthesis of 2-azabicyclo[3.3.1]nonane ring system such as I [R = n-pentyl, Bn, Ts, etc.] from simple pyrroles, employing a combined photochem./palladium-catalyzed approach was reported. Substrate scope was broad, allowing incorporation of a wide range of functionality relevant to medicinal chem. Mechanistic studies demonstrated that process occurs by acid-assisted C-N bond cleavage followed by β-hydride elimination to form a reactive diene, demonstrated that efficient control of what might be considered off-cycle reactions can result in productive tandem catalytic processes. This represented a short and versatile route to biol. important morphan scaffold. In the experiment, the researchers used many compounds, for example, (5-Fluoro-2-iodophenyl)methanol (cas: 877264-43-2SDS of cas: 877264-43-2).

(5-Fluoro-2-iodophenyl)methanol (cas: 877264-43-2) 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. A typical method for synthesis of aromatic iodides is diazotization of primary aromatic amines followed by treatment of potassium iodide. Aliphatic alcohols are converted to alkyl iodides by treating with hydrogen iodide.SDS of cas: 877264-43-2

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

Substituent Effect on the Optoelectronic Properties of Alternating Fluorene-Cyclopentadithiophene Copolymers was written by Pal, Bikash;Yen, Wei-Che;Yang, Jye-Shane;Chao, Chi-Yang;Hung, Ying-Chieh;Lin, Shiang-Tai;Chuang, Chia-Hao;Chen, Chun-Wei;Su, Wei-Fang. And the article was included in Macromolecules (Washington, DC, United States) in 2008.COA of Formula: C9H4I2OS2 This article mentions the following:

A novel series of soluble alternating conjugated copolymers, comprised of 9,9-dihexylfluorene and cyclopentadithiophenes (P1-P5), were synthesized via Pd-catalyzed Suzuki coupling reaction in good yields. The UV-vis absorption spectra, fluorescence spectra, fluorescence quantum yields, and cyclic voltammograms of P1-P5 are also reported. The P2 and P3 with electron-donating non-π-substituents (ethylenedioxy and propylenedioxy bridges the 3,3-positions of the thiophene groups) display high fluorescence quantum yields and red-shifted absorption as compared with nonsubstituted P1. However, the P4 and P5 are weakly fluorescent and exhibit blue-shifted absorption which are due to the presence of electron-withdrawing π-substituents (carbonyl and dicyanoethenyl). The behavior of P4 and P5 can be attributed to the significant electronic coupling between the π-substituents and the conjugated polymer backbone that leads to a less allowed optical transition between the ground and the lowest excited state, resembling the meta conjugation effect in phenylene-derived conjugated π-systems. This argument is supported by MO distribution calculations In the experiment, the researchers used many compounds, for example, Bis(2-iodothiophen-3-yl)methanone (cas: 474416-61-0COA of Formula: C9H4I2OS2).

Bis(2-iodothiophen-3-yl)methanone (cas: 474416-61-0) belongs to iodide derivatives. Iodide-containing intermediates are common in organic synthesis, because of the easy formation and cleavage of the C–I bond. 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.COA of Formula: C9H4I2OS2

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

Steroidal Wheel-and-Axle Host Type Molecules: Insights from Awkward Shape, Conformation, Z’ > 1 and Packing was written by Ramirez-Montes, Pedro I.;Ochoa, Maria E.;Santillan, Rosa;Ramirez, Daniel J.;Farfan, Norberto. And the article was included in Crystal Growth & Design in 2014.Safety of 1,2-Difluoro-3-iodobenzene This article mentions the following:

The synthesis and crystal structure of three new mol. rotors I,II,III , derived from levonorgestrel and norethisterone are reported. The conformation, close contacts, and shape characteristics of these mols. exhibiting Z’ = 2 and the inclusion of solvent mols. were analyzed together with the crystal structures of parent mols. retrieved from the Cambridge Structural Database. For the set of estranes studied, we confirmed that whenever an alternative conformer cannot satisfy the crystallog. symmetry, a second mol. is incorporated in the asym. unit resulting in conformational isomorphism (Z’ > 1). The shape of these mols. could make them interesting as potential hosts. In the experiment, the researchers used many compounds, for example, 1,2-Difluoro-3-iodobenzene (cas: 64248-57-3Safety of 1,2-Difluoro-3-iodobenzene).

1,2-Difluoro-3-iodobenzene (cas: 64248-57-3) 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. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.Safety of 1,2-Difluoro-3-iodobenzene

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

A formal synthesis of crinipellin B based on the arene-alkane meta-photocycloaddition reaction was written by Wender, Paul A.;Dore, Timothy M.. And the article was included in Tetrahedron Letters in 1998.SDS of cas: 133232-56-1 This article mentions the following:

Starting from tri-Et phosphonopropionate and 3-nitro-2-methylbenzoic acid, a formal synthesis of crinipellin B was achieved. The strategy draws on the use of a novel version of the arene-alkene meta-photocycloaddition reaction that proceeds with the generation of 4 rings and 4 quaternary stereocenters in one synthetic operation. In the experiment, the researchers used many compounds, for example, 3-Iodo-2-methylbenzoic acid (cas: 133232-56-1SDS of cas: 133232-56-1).

3-Iodo-2-methylbenzoic acid (cas: 133232-56-1) belongs to iodide derivatives. Iodide-containing intermediates are common in organic synthesis, because of the easy formation and cleavage of the C–I bond. 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. This periodic order also follows the atomic radius of halogens and the length of the carbon-halogen bond.SDS of cas: 133232-56-1

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

Palladium-catalyzed alkoxycarbonylation of unactivated secondary alkyl bromides at low pressure was written by Sargent, Brendon T.;Alexanian, Erik J.. And the article was included in Journal of the American Chemical Society in 2016.Product Details of 77350-52-8 This article mentions the following:

Catalytic carbonylations of organohalides are important C-C bond formations in chem. synthesis. Carbonylations of unactivated alkyl halides remain a challenge and currently require the use of alkyl iodides under harsh conditions and high pressures of CO. Herein we report a palladium-catalyzed alkoxycarbonylation of secondary alkyl bromides that proceeds at low pressure (2 atm CO) under mild conditions. Preliminary mechanistic studies are consistent with a hybrid organometallic-radical process. These reactions efficiently deliver esters from unactivated alkyl bromides across a diverse range of substrates and represent the first catalytic carbonylations of alkyl bromides with carbon monoxide. In the experiment, the researchers used many compounds, for example, N,N-Diethyl-4-iodobenzamide (cas: 77350-52-8Product Details of 77350-52-8).

N,N-Diethyl-4-iodobenzamide (cas: 77350-52-8) belongs to iodide derivatives. Iodide-containing intermediates are common in organic synthesis, because of the easy formation and cleavage of the C–I bond. 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. This periodic order also follows the atomic radius of halogens and the length of the carbon-halogen bond.Product Details of 77350-52-8

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

A bright two-photon fluorescent probe for real-time monitoring autophagy in living cells was written by Jiang, Chuankun;Li, Longchun;Jiang, Jiacheng;Hou, Lilin;Fang, Gemin;Haizhu, Yu;Meng, Xiangming. And the article was included in Chinese Chemical Letters in 2020.Synthetic Route of C7H5IO2 This article mentions the following:

A novel donor-acceptor (D-A) type of two-photon (TP) fluorescent probe, i.e. Lyso-OSC, based on the lysosome-targeting morpholine group was developed. The polarity sensing coumarin group was functionalized as the acceptor and the 1-vinyl-4-methoxybenzene group was engineered as the donor. The fluorescence intensity and emission maximum wavelength of Lyso-OSC are highly sensitive to the polarity changes of solvent. The two-photon absorption cross-section and tissue penetration depth are up to 254 GM and 150μm, resp. The strong fluorescence, high sensitivity to polarity, low cytotoxicity, and accurate lysosome-targeting ability entail Lyso-OSC the excellent performance in detecting the polarity changes of cellular environment. To this end, a bright, real-time imaging autophagy of living cells has been achieved. In the experiment, the researchers used many compounds, for example, 4-Hydroxy-2-iodobenzaldehyde (cas: 90151-01-2Synthetic Route of C7H5IO2).

4-Hydroxy-2-iodobenzaldehyde (cas: 90151-01-2) 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.Synthetic Route of C7H5IO2

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

First metalation of aryl iodides: directed ortho-lithiation of iodopyridines, halogen-dance, and application to synthesis was written by Rocca, P.;Cochennec, C.;Marsais, F.;Thomas-dit-Dumont, L.;Mallet, M.;Godard, A.;Queguiner, G.. And the article was included in Journal of Organic Chemistry in 1993.Quality Control of 2-Chloro-4-iodo-3-methylpyridine This article mentions the following:

Metalation of iodopyridines was successfully achieved by LDA at low temperature In many cases, lithiation is ortho directed by the iodo group which subsequently ortho-migrates very fast to give stabilized iodolithiopyridines. This procedure was applied to 2-fluoro- and 2-chloro-3-iodopyridines, 3-fluoro-4-iodopyridine, and 2-chloro-3-fluoro-4-iodopyridine. The resulting lithio intermediates were obtained in high yields before being reacted with electrophiles leading to various polysubstituted pyridines. Some of these iodopyridines were used as key mols. for the preparation of fused polyaromatic alkaloids. Thus, perlolidine (I), δ-carbolines, and 2,10-diazaphenanthrenes were readily prepared in few steps taking advantage of the iodo reactivity for heteroring cross-coupling. Coupling of [2-(pivaloylamino)phenyl]boronic acid with 2-fluoro-4-iodo-3-pyridinecarboxaldehyde gave I. In the experiment, the researchers used many compounds, for example, 2-Chloro-4-iodo-3-methylpyridine (cas: 153034-88-9Quality Control of 2-Chloro-4-iodo-3-methylpyridine).

2-Chloro-4-iodo-3-methylpyridine (cas: 153034-88-9) belongs to iodide derivatives. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. 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.Quality Control of 2-Chloro-4-iodo-3-methylpyridine

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

A general carbonyl alkylative amination for tertiary amine synthesis was written by Kumar, Roopender;Floden, Nils J.;Whitehurst, William G.;Gaunt, Matthew J.. And the article was included in Nature (London, United Kingdom) in 2020.Quality Control of 1-Bromo-4-(2-iodoethyl)benzene This article mentions the following:

The ubiquity of tertiary alkylamines in pharmaceutical and agrochem. agents, natural products and small-mol. biol. probes has stimulated efforts towards their streamlined synthesis. Arguably the most robust method for the synthesis of tertiary alkylamines is carbonyl reductive amination, which comprises two elementary steps: the condensation of a secondary alkylamine with an aliphatic aldehyde to form an all-alkyl-iminium ion, which is subsequently reduced by a hydride reagent. Direct strategies were sought for a ‘higher order’ variant of this reaction via the coupling of an alkyl fragment with an alkyl-iminium ion that was generated in situ. However, despite extensive efforts, the successful realization of a ‘carbonyl alkylative amination’ has not yet been achieved. Here the authors present a practical and general synthesis of tertiary alkylamines through the addition of alkyl radicals to all-alkyl-iminium ions. The process is facilitated by visible light and a silane reducing agent, which trigger a distinct radical initiation step to establish a chain process. This operationally straightforward, metal-free and modular transformation forms tertiary amines, without structural constraint, via the coupling of aldehydes and secondary amines with alkyl halides. The structural and functional diversity of these readily available precursors provides a versatile and flexible strategy for the streamlined synthesis of complex tertiary amines. In the experiment, the researchers used many compounds, for example, 1-Bromo-4-(2-iodoethyl)benzene (cas: 85356-68-9Quality Control of 1-Bromo-4-(2-iodoethyl)benzene).

1-Bromo-4-(2-iodoethyl)benzene (cas: 85356-68-9) belongs to iodide derivatives. Generally organic iodides can be divided into two classes of alkyl iodides and aryl iodides. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. 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.Quality Control of 1-Bromo-4-(2-iodoethyl)benzene

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