Tag: 200-300

Palladium-Catalyzed Chlorocarbonylation of Aryl (Pseudo)Halides Through In Situ Generation of Carbon Monoxide was written by Boehm, Philip;Roediger, Sven;Bismuto, Alessandro;Morandi, Bill. And the article was included in Angewandte Chemie, International Edition in 2020.Recommanded Product: 4-Iodo-1,2-dimethoxybenzene This article mentions the following:

An efficient palladium-catalyzed chlorocarbonylation of aryl (pseudo)halides that gives access to a wide range of carboxylic acid derivatives has been developed. The use of butyryl chloride as a combined CO and Cl source eludes the need for toxic, gaseous carbon monoxide, thus facilitating the synthesis of high-value products from readily available aryl (pseudo)halides. The combination of palladium(0), Xantphos, and an amine base is essential to promote this broadly applicable catalytic reaction. Overall, this reaction provides access to a great variety of carbonyl-containing products through in situ transformation of the generated aroyl chloride. Combined exptl. and computational studies support a reaction mechanism involving in situ generation of CO. In the experiment, the researchers used many compounds, for example, 4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2Recommanded Product: 4-Iodo-1,2-dimethoxybenzene).

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. 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.Recommanded Product: 4-Iodo-1,2-dimethoxybenzene

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

Synthesis and Biological Profiling of Pyrazolo-Fused 7-Deazapurine Nucleosides was written by Fleuti, Marianne;Bartova, Katerina;Slavetinska, Lenka Postova;Tloust’ova, Eva;Tichy, Michal;Gurska, Sona;Pavlis, Petr;Dzubak, Petr;Hajduch, Marian;Hocek, Michal. And the article was included in Journal of Organic Chemistry in 2020.Related Products of 34091-51-5 This article mentions the following:

A series of 8-substituted 1-methyl-1,4-dihydropyrazolo[3′,4′:4,5]pyrrolo[2,3-d]pyrimidine (methylpyrazolo-fused 7-deazapurine) ribonucleosides has been designed and synthesized. Two synthetic approaches to the key heterocyclic aglycon I, (i) a six-step classical heterocyclization starting from 5-chloro-1-methyl-4-nitropyrazole and (ii) a three-step cross-coupling and cyclization approach starting from the zinc 4,6-dichloropyrimidine, gave comparable total yield of 18% vs. 13%. The glycosylation of I was attempted by three different methods but only the Vorbruggen silyl-base protocol was efficient and stereoselective to give desired β-anomeric nucleoside intermediate. Its nucleophilic substitutions or cross-coupling reactions at position 8 and deprotection of the sugar moiety gave eight derivatives of pyrazolo-fused deazapurine ribonucleosides, e.g. II, some of which were weakly fluorescent. Me, amino and methylsulfanyl derivatives exerted sub-micromolar cytotoxic effects in vitro against a panel of cancer and leukemia cell lines, as well as antiviral effect against hepatitis C virus in the replicon assay. In the experiment, the researchers used many compounds, for example, 5-Iodo-1-methyl-1H-pyrazole (cas: 34091-51-5Related Products of 34091-51-5).

5-Iodo-1-methyl-1H-pyrazole (cas: 34091-51-5) 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.Related Products of 34091-51-5

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

Convenient Access to Arylated Spirocyclic Bisphosphonates was written by Lord, Taylor M.;Casino, Stephanie L.;Hartzell, Susan E.;Garcia, Kevin J.;Pike, Robert D.;Stockland, Robert A. Jr.. And the article was included in ChemistrySelect in 2016.Category: iodides-buliding-blocks This article mentions the following:

The synthesis of P-arylated spirocyclic bisphosphonates is described. The title compounds were generated through a process that combined transesterification with a palladium catalyzed P-arylation. The cross-coupling step could be carried out at room temperature using aryl iodides, while analogous reactions involving aryl bromides required heating. Nitrogen, oxygen, and sulfur containing heterocycles were also successfully incorporated into the framework. Using this approach 20 new arylated compounds were generated bearing a range of electrophiles and functional groups. For the more reactive aryl iodides, the catalyst loading could be decreased to 0.3 % Pd per P-H group in scaled-up versions of the method. The two-step process does not require the use of chlorophosphorus reagents. In the experiment, the researchers used many compounds, for example, 3-Iodobenzo[b]thiophene (cas: 36748-88-6Category: iodides-buliding-blocks).

3-Iodobenzo[b]thiophene (cas: 36748-88-6) 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. 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.Category: iodides-buliding-blocks

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

Silicon-Directed Oxa-Pictet-Spengler Cyclization and an Unusual Dimerization of 2-Trimethylsilanyl Tryptophols was written by Zhang, Xuqing;Li, Xiaojie;Lanter, James C.;Sui, Zhihua. And the article was included in Organic Letters in 2005.SDS of cas: 220185-63-7 This article mentions the following:

The tetrahydropyrano[3,4-b]indoles I (n = 1, 2; R¹ = H, CN, Cl, NO₂, F, CF₃, CO₂Me; R² = H, CF₃, Cl; R³ = Me; R⁴ = Me, MeS, EtS, BnS) were synthesized from 2-(2-trimethylsilanyl-1H-indol-3-yl)alkanols II and various ketones or aldehydes through silicon-directed oxa-Pictet-Spengler cyclizations. An unusual reaction led to the dimeric products III when some of II was treated with acetone using BF₃ as the catalyst. In the experiment, the researchers used many compounds, for example, 4,5-Dichloro-2-iodoaniline (cas: 220185-63-7SDS of cas: 220185-63-7).

4,5-Dichloro-2-iodoaniline (cas: 220185-63-7) 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. 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.SDS of cas: 220185-63-7

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

Cross-Coupling of [2-Aryl-1,1,2,2-tetrafluoroethyl](trimethyl)silanes with Aryl Halides was written by O’Duill, Miriam;Dubost, Emmanuelle;Pfeifer, Lukas;Gouverneur, Veronique. And the article was included in Organic Letters in 2015.Synthetic Route of C8H9IO2 This article mentions the following:

The synthesis of arylCF₂CF₂SiMe₃ and their reactivity in cross-coupling reactions with aryl iodides and aryl bromides to afford a range of 1,1,2,2-tetrafluoro-1,2-diarylethanes is reported. The use of pyridine as an alternative to phenanthroline, and the ability to carry out the reaction at 60 °C or room temperature are the key features of this Cu-Ag mediated cross-coupling methodol. The chem. is compatible with (hetero)aryl halides, offering a platform to develop products of interest in material and medicinal chem. Thus, e.g, cross-coupling of silane I with aryl iodide II under optimized conditions consisting of CuI (1 equiv), AgF (1.5 equiv) and pyridine (5.0 equiv) in DMSO at 60° for 6 h afforded III (76%). In the experiment, the researchers used many compounds, for example, 4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2Synthetic Route of C8H9IO2).

4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2) 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. 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.Synthetic Route of C8H9IO2

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

β-Lactams with antiproliferative and antiapoptotic activity in breast and chemoresistant colon cancer cells was written by Malebari, Azizah M.;Fayne, Darren;Nathwani, Seema M.;O’Connell, Fiona;Noorani, Sara;Twamley, Brendan;O’Boyle, Niamh M.;O’Sullivan, Jacintha;Zisterer, Daniela M.;Meegan, Mary J.. And the article was included in European Journal of Medicinal Chemistry in 2020.Electric Literature of C8H7IO2 This article mentions the following:

A series of novel 1,4-diaryl-2-azetidinone analogs of combretastatin A-4 (CA-4) have been designed, synthesized and evaluated in vitro for antiproliferative activity, antiapoptotic activity and inhibition of tubulin polymerization Glucuronidation of CA-4 by uridine 5-diphosphoglucuronosyl transferase enzymes (UGTs) has been identified as a mechanism of resistance in cancer cells. Potential sites of ring B glucuronate conjugation are removed by replacing the B ring meta-hydroxy substituent of selected series of β-lactams with alternative substituents e.g., F, Cl, Br, I, and Me. The 3-phenyl-β-lactam I (R¹ = Ph) and 3-hydroxy-β-lactam I (R¹ = OH) (II) demonstrate improved activity over CA-4 in CA-4 resistant HT-29 colon cancer cells (IC₅₀ = 9 nM and 3 nM, resp., compared with IC₅₀ = 4.16μM for CA-4), while retaining potency in MCF-7 breast cancer cells (IC₅₀ = 17 nM and 22 nM, resp., compared with IC₅₀ = for 4 nM for CA-4). Compound II binds at the colchicine site of tubulin, and strongly inhibits tubulin assembly at micromolar concentrations comparable to CA-4. In addition, compound II induced mitotic arrest at low concentration in both cell lines MCF-7 and HT-29 together with down-regulation of expression of antiapoptotic proteins Mcl-1, Bcl-2 and survivin in MCF-7 cells. These novel antiproliferative and antiapoptotic β-lactams are potentially useful scaffolds in the development of tubulin-targeting agents for the treatment of breast cancers and chemoresistant colon cancers. In the experiment, the researchers used many compounds, for example, 3-Iodo-4-methoxybenzaldehyde (cas: 2314-37-6Electric Literature of C8H7IO2).

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.Electric Literature of C8H7IO2

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

Cu-Catalyzed Enantioselective Ring Opening of Cyclic Diaryliodoniums toward the Synthesis of Chiral Diarylmethanes was written by Li, Bin;Chao, Zengyin;Li, Chunyu;Gu, Zhenhua. And the article was included in Journal of the American Chemical Society in 2018.Product Details of 877264-43-2 This article mentions the following:

A Cu-catalyzed enantioselective desymmetrizing ring-opening reaction of six-membered cyclic diaryliodonium salts with carboxylic acids or thioacids is reported for the facile access to chiral diarylmethanes. A Cu/[cyclopropyl bis(oxazoline)] catalyst well discriminates two C-I bonds of prochiral cyclic diaryliodonium salts. A stereochem. model was proposed to rationalize the stereochem. outcome on the basis of the crystal structure of cyclic diaryliodonium salt. In the experiment, the researchers used many compounds, for example, (5-Fluoro-2-iodophenyl)methanol (cas: 877264-43-2Product Details of 877264-43-2).

(5-Fluoro-2-iodophenyl)methanol (cas: 877264-43-2) 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. 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.Product Details of 877264-43-2

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

Organic iodine compounds in fine particulate matter from a continental urban region: Insights into secondary formation in the atmosphere was written by Shi, Xiaodi;Qiu, Xinghua;Chen, Qi;Chen, Shiyi;Hu, Min;Rudich, Yinon;Zhu, Tong. And the article was included in Environmental Science & Technology in 2021.Related Products of 5460-32-2 This article mentions the following:

Atm. iodine chem. can significantly affect the atm. oxidation capacity in certain regions. In such processes, particle-phase organic iodine compounds (OICs) are key reservoir species in their loss processes. However, their presence and formation mechanism remain unclear, especially in continental regions. Using gas chromatog. and time-of-flight mass spectrometry coupled with both electron capture neg. ionization and electron impact sources, this study systematically identified unknown OICs in 2-yr samples of ambient fine particulate matter (PM_2.5) collected in Beijing, an inland city. We determined the mol. structure of 37 unknown OICs, among which six species were confirmed by reference standards The higher concentrations for ∑₃₇OICs (median: 280 pg m^-3; range: 49.0-770 pg m^-3) measured in the heating season indicate intensive coal combustion sources of atm. iodine. 1-Iodo-2-naphthol and 4-iodoresorcinol are the most abundant species mainly from primary combustion emission and secondary formation, resp. The detection of 2- and 4-iodoresorcinols, but not of iodine-substituted catechol/hydroquinone or 5-iodoresorcinol, suggests that they are formed via the electrophilic substitution of resorcinol by hypoiodous acid, a product of the reaction of iodine with ozone. This study reports isomeric information on OICs in continental urban PM_2.5 and provides valuable evidence on the formation mechanism of OICs in ambient particles. In the experiment, the researchers used many compounds, for example, 4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2Related Products of 5460-32-2).

4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2) belongs to iodide derivatives. 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.Related Products of 5460-32-2

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

Leoligin-inspired synthetic lignans with selectivity for cell-type and bioactivity relevant for cardiovascular disease was written by Linder, Thomas;Liu, Rongxia;Atanasov, Atanas G.;Li, Yuanfang;Geyrhofer, Sophie;Schwaiger, Stefan;Stuppner, Hermann;Schnuerch, Michael;Dirsch, Verena M.;Mihovilovic, Marko D.. And the article was included in Chemical Science in 2019.Formula: C8H9IO2 This article mentions the following:

Recently, a natural compound leoligin, a furan-type lignan, was discovered as an interesting hit compound with an anti-inflammatory pharmacol. activity profile. We developed a modular and stereoselective approach for the synthesis of the edelweiss-derived lignan leoligin and used the synthetic route to rapidly prepare leoligin analogs even on the gram scale. Proof of concept of this approach together with cell-based bio-assays gained structural analogs with increased selectivity towards vascular smooth muscle vs. endothelial cell proliferation inhibition, a major benefit in fighting vascular neointima formation. In addition, we identified the structural features of leoligin analogs that define their ability to inhibit the pro-inflammatory NF-κB pathway. Results are discussed in the context of structural modification of these novel synthetic lignans. 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. Organic iodides are widely used in organic synthesis. Halogenation of aromatic hydrocarbons is a very important reaction via an electrophilic aromatic substitution. 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.Formula: C8H9IO2

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

A dual light-driven palladium catalyst: Breaking the barriers in carbonylation reactions was written by Torres, Gerardo M.;Liu, Yi;Arndtsen, Bruce A.. And the article was included in Science (Washington, DC, United States) in 2020.Application In Synthesis of 1-Chloro-4-iodobutane This article mentions the following:

Transition metal-catalyzed coupling reactions have become one of the most important tools in modern synthesis. However, an inherent limitation to these reactions is the need to balance operations, because the factors that favor bond cleavage via oxidative addition ultimately inhibit bond formation via reductive elimination. Here, we describe an alternative strategy that exploits simple visible-light excitation of palladium to drive both oxidative addition and reductive elimination with low barriers. Palladium-catalyzed carbonylations can thereby proceed under ambient conditions, with challenging aryl or alkyl halides and difficult nucleophiles, and generate valuable carbonyl derivatives such as acid chlorides, esters, amides, or ketones in a now-versatile fashion. Mechanistic studies suggest that concurrent excitation of palladium(0) and palladium(II) intermediates is responsible for this activity. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9Application In Synthesis of 1-Chloro-4-iodobutane).

1-Chloro-4-iodobutane (cas: 10297-05-9) 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. 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.Application In Synthesis of 1-Chloro-4-iodobutane

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