Author: Jessica.F

Asymmetric synthesis of protected unnatural α-amino acids via enantioconvergent nickel-catalyzed cross-coupling was written by Yang, Ze-Peng;Freas, Dylan J.;Fu, Gregory C.. And the article was included in Journal of the American Chemical Society in 2021.Category: iodides-buliding-blocks This article mentions the following:

Interest in unnatural α-amino acids has increased rapidly in recent years in areas ranging from protein design to medicinal chem. to materials science. Consequently, the development of efficient, versatile, and straightforward methods for their enantioselective synthesis is an important objective in reaction development. In this report, we establish that a chiral catalyst based on nickel, an earth-abundant metal, can achieve the enantioconvergent coupling of readily available racemic alkyl electrophiles with a wide variety of alkylzinc reagents (1:1.1 ratio) to afford protected unnatural α-amino acids in good yield and ee. This cross-coupling, which proceeds under mild conditions and is tolerant of air, moisture, and a broad array of functional groups, complements earlier approaches to the catalytic asym. synthesis of this valuable family of mols. We have applied our new method to the generation of several enantioenriched unnatural α-amino acids that have previously been shown to serve as useful intermediates in the synthesis of bioactive compounds In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9Category: iodides-buliding-blocks).

1-Chloro-4-iodobutane (cas: 10297-05-9) 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. 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.Category: iodides-buliding-blocks

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

Double-fold C-H oxygenation of arenes using PyrDipSi: a general and efficient traceless/modifiable silicon-tethered directing group was written by Gulevich, Anton V.;Melkonyan, Ferdinand S.;Sarkar, Dhruba;Gevorgyan, Vladimir. And the article was included in Journal of the American Chemical Society in 2012.Recommanded Product: 77350-52-8 This article mentions the following:

The efficient Pd-catalyzed double-fold C-H oxygenation of arenes into resorcinols e. g., I using the newly developed 2-pyrimidyldiisopropylsilyl (PyrDipSi) directing group is described. Its use allows for the sequential introduction of OAc and OPiv groups in a one-pot manner to produce orthogonally protected resorcinol derivatives The PyrDipSi group is superior to the previously developed 2-pyridyldiisopropylsilyl (PyDipSi) group, as it is efficient for monooxygenation of ortho-substituted arenes. Notably, the PyrDipSi group can be easily installed into arene mols. and can be easily removed or modified after the oxygenation reaction. In the experiment, the researchers used many compounds, for example, N,N-Diethyl-4-iodobenzamide (cas: 77350-52-8Recommanded Product: 77350-52-8).

N,N-Diethyl-4-iodobenzamide (cas: 77350-52-8) 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.Recommanded Product: 77350-52-8

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

Synthesis of novel heterocyclic 3-aryl-2-butenoic acid retinoids was written by Gale, Jonathan B.;Calvo Vega, Mario. And the article was included in Ingenieria y Ciencia Quimica in 1997.Recommanded Product: 3-Iodo-2-methylbenzoic acid This article mentions the following:

Several heterocyclic benzophenone-like retinoids e.g. I (R = R¹ = H; R = H, R¹ = Me; R = Me, R¹ = H; X = O, CH₂) containing a terminal methylcinnamic acid moiety were prepared The compounds were designed to mimic either all-trans retinoic acid or 9-cis retinoic acid, depending on the Me substitution pattern of the aromatic ring closest to the terminal carboxyl group. The syntheses consist of three or four steps starting from a known core benzothienyl system via a Heck-type aryl-vinyl coupling reaction. In the experiment, the researchers used many compounds, for example, 3-Iodo-2-methylbenzoic acid (cas: 133232-56-1Recommanded Product: 3-Iodo-2-methylbenzoic acid).

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. 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.Recommanded Product: 3-Iodo-2-methylbenzoic acid

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

Proton Transfer Can Govern Regioselectivity Assisted by Iron Catalysis was written by Li, Yudong;Fu, Liyan;Jiang, Xiaolin;Zhao, Dongmei;Wang, Hui-Fang;Xia, Chungu;Li, Yuehui. And the article was included in iScience in 2020.Application of 207115-22-8 This article mentions the following:

Ortho-selective aromatic C-H functionalization is frequently used in organic synthesis and chem./pharmaceutical industries. However, this reaction relies heavily on the use of directing groups suffering from limited substrate scope and extra steps to put on and remove the directing/protecting groups. Herein authors present the previously neglected concept that enables good to nearly complete selective ortho position. Proton transfer was utilized to tune the electron d. on the aryl ring and determine the positional selectivity of electrophilic substitution. Consistently with deuteration experiments and DFT studies, this work demonstrates that acid-promoted proton transfer directs accelerated ortho-selective halogenation of NH/OH contained aromatic amines/phenols with excellent selectivity (>40 examples; up to 98:2 ortho/para selectivity). The application potential of this Fe-catalyzed method is demonstrated by the convenient synthesis of three alkaloids and tizanidine. This report raises the possibility that proton transfer could serve as the basis of developing new selective C-H functionalization reactions. In the experiment, the researchers used many compounds, for example, 4-Bromo-2-iodophenol (cas: 207115-22-8Application of 207115-22-8).

4-Bromo-2-iodophenol (cas: 207115-22-8) 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.Application of 207115-22-8

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

Palladium-catalyzed asymmetric coupling cyclization of terminal γ-allenols with aryl iodides was written by Xie, Xi;Ma, Shengming. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2013.Quality Control of N,N-Diethyl-4-iodobenzamide This article mentions the following:

A Pd-catalyzed asym. coupling cyclization of γ-allenols with aryl iodides has been developed. α-(Tetrahydrofuran-2-yl)styrene derivatives can be prepared in 60-86% yields with ee values ranging from 85-92%. In the experiment, the researchers used many compounds, for example, N,N-Diethyl-4-iodobenzamide (cas: 77350-52-8Quality Control of N,N-Diethyl-4-iodobenzamide).

N,N-Diethyl-4-iodobenzamide (cas: 77350-52-8) 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. This periodic order also follows the atomic radius of halogens and the length of the carbon-halogen bond.Quality Control of N,N-Diethyl-4-iodobenzamide

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

Cobalt-catalysed enantioselective C(sp³)-C(sp³) coupling was written by Li, Yan;Nie, Wan;Chang, Zhe;Wang, Jia-Wang;Lu, Xi;Fu, Yao. And the article was included in Nature Catalysis in 2021.Recommanded Product: 10297-05-9 This article mentions the following:

Enantioselective C(sp³)-C(sp³) coupling substantially impacts organic synthesis but remains challenging. Cobalt has played an important role in the development of homogeneous organometallic catalysis, but there are few examples of its use in asym. cross-coupling. Here, a cobalt-catalyzed enantioselective C(sp³)-C(sp³) coupling reaction, namely, alkene hydroalkylation, to access chiral fluoroalkanes was reported. This reaction represents a catalyst-controlled enantioselective coupling mode in which a tailor-made auxiliary is unnecessary; via this reaction, an aliphatic C-F stereogenic center can be introduced at the desired position in an alkyl chain. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9Recommanded Product: 10297-05-9).

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.Recommanded Product: 10297-05-9

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

Modulation of π-electron conjugation in oligo(triacetylene) chromophores by incorporation of a central spacer was written by Martin, Rainer E.;Wytko, Jennifer A.;Diederich, Francois;Boudon, Corinne;Gisselbrecht, Jean-Paul;Gross, Maurice. And the article was included in Helvetica Chimica Acta in 1999.Synthetic Route of C10H12I2 This article mentions the following:

A series of trimeric hybrid oligomers was prepared by insertion of different hetero-spacers between two (E)-hex-3-ene-1,5-diyne (E = 1,2-diethynylethene, DEE) moieties, and the optical and electrochem. properties of the resulting π-conjugated materials were compared to those of the DEE dimer and trimer, which formally contain a DEE moiety as homo-spacer. The hetero-spacers were: benzenoid (phenylene, naphthalene, biphenylene, anthracene), π-electron-deficient (pyrazine, pyridine) and π-electron-rich (thiophene, furan) aromatic rings, and trans-Pt(PEt₃)₂. The hybrid oligomers were synthesized using the method of K. Sonogashira et al. (1978), i.e., cross-coupling between mono-deprotected DEE and the appropriately bis-functionalized spacer. UV/VIS data revealed that the majority of the hetero-spacers were less effective than the homo-spacer DEE in facilitating π-electron delocalization along the linearly conjugated oligomeric backbone. With increasing degree of benzenoid aromaticity in the hetero-spacer, the electronic communication between the terminal DEE moieties in the hybrid oligomers was reduced. As a remarkable exception, a large bathochromic shift of the longest-wavelength absorption maximum, which is indicative of enhanced π-electron delocalization, was obtained upon introducing an anthracene-9,10-diyl moiety as hetero-spacer. Electrochem. studies by cyclic and steady-state voltammetry confirmed the limited extent of π-electron delocalization in the majority of the hybrid oligomers. The fluorescence properties of many of the DEE hybrid materials were dramatically enhanced upon incorporation of the heterospacers. The heterocyclic derivatives containing pyridine, pyrazine, or thiophene spacers, resp., displayed a strong fluorescence emission, demonstrating the value of combining repeat units to modulate oligomeric and polymeric properties. The pyridine derivative provided an interesting example of a mol. system, in which both the electronic absorption and emission characteristics can be reversibly switched as a function of pH. In the experiment, the researchers used many compounds, for example, 1,4-Diiodo-2,3,5,6-tetramethylbenzene (cas: 3268-21-1Synthetic Route of C10H12I2).

1,4-Diiodo-2,3,5,6-tetramethylbenzene (cas: 3268-21-1) belongs to iodide derivatives. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.Synthetic Route of C10H12I2

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

Palladium-Catalyzed Direct Oxidative Coupling of Iodoarenes with Primary Alcohols Leading to Ketones: Application to the Synthesis of Benzofuranones and Indenones was written by Suchand, Basuli;Sreenivasulu, Chinnabattigalla;Satyanarayana, Gedu. And the article was included in European Journal of Organic Chemistry in 2019.Reference of 5460-32-2 This article mentions the following:

In the present study, a palladium-catalyzed direct oxidative acylation through cross-dehydrogenative coupling has been investigated, utilizing readily available primary alcs. as acylating sources. Overall, this oxidative coupling proceeds via three distinct transformations such as oxidation, radical formation, and cross-coupling in one catalytic process. This protocol does not involve the assistance of a directing group or activation of the carbonyl group by any other means. Furthermore, this reaction made use of no toxic CO gas as carbonylating agent; instead, feedstock primary alcs. have been utilized as acylation source. Notably, the synthesis of benzofuranones and indenones is enabled. This strategy was also applied to the synthesis of n-butylphthalide, fenofibrate, pitofenone, and neo-lignan. Thus, e.g., Me 2-iodobenzoate + benzyl alc. → Me 2-benzoylbenzoate (64%) in presence of Pd(OAc)₂, Ag₂O and TBHP. In the experiment, the researchers used many compounds, for example, 4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2Reference of 5460-32-2).

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. 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.Reference of 5460-32-2

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

Synthesis and biological evaluation of novel flexible nucleoside analogues that inhibit flavivirus replication in vitro was written by Thames, Joy E.;Waters, Charles D. III;Valle, Coralie;Bassetto, Marcella;Aouadi, Wahiba;Martin, Baptiste;Selisko, Barbara;Falat, Arissa;Coutard, Bruno;Brancale, Andrea;Canard, Bruno;Decroly, Etienne;Seley-Radtke, Katherine L.. And the article was included in Bioorganic & Medicinal Chemistry in 2020.Safety of 4,5-Diiodo-1H-imidazole This article mentions the following:

Flaviviruses, such as Dengue (DENV) and Zika (ZIKV) viruses, represent a severe health burden. There are currently no FDA-approved treatments, and vaccines against most flaviviruses are still lacking. We have developed several flexible analogs (“fleximers”) of the FDA-approved nucleoside Acyclovir that exhibit activity against various RNA viruses, demonstrating their broad-spectrum potential. The current study reports activity against DENV and Yellow Fever Virus (YFV), particularly for compound 1. Studies to elucidate the mechanism of action suggest the flex-analog triphosphates, especially 1-TP, inhibit DENV and ZIKV methyltransferases, and a secondary, albeit weak, effect on the DENV RNA-dependent RNA polymerase was observed at high concentrations The results of these studies are reported herein. In the experiment, the researchers used many compounds, for example, 4,5-Diiodo-1H-imidazole (cas: 15813-09-9Safety of 4,5-Diiodo-1H-imidazole).

4,5-Diiodo-1H-imidazole (cas: 15813-09-9) belongs to iodide derivatives. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine. 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.Safety of 4,5-Diiodo-1H-imidazole

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

Three chloro(trifluoromethyl)pyridines as model substrates for regioexhaustive functionalization was written by Cottet, Fabrice;Schlosser, Manfred. And the article was included in European Journal of Organic Chemistry in 2004.Name: 2-Chloro-5-(trifluoromethyl)-4-iodopyridine This article mentions the following:

As a further test of the concept of regioexhaustive functionalization, 2-chloro-6-(trifluoromethyl)pyridine, 2-chloro-5-(trifluoromethyl)pyridine and 3-chloro-4-(trifluoromethyl)pyridine were each converted into the three possible carboxylic acids. This was achieved by employing several, but not all of the organometallic “toolbox methods”; transformation of a more basic organometallic species into a less basic isomer by transmetalation-equilibration, site discriminating deprotonation with lithium N,N-diisopropylamide or lithium 2,2,6,6-tetramethylpiperidide, regio-divergent iodine migration and steric screening of acidic positions by a bulky trialkylsilyl group. In the experiment, the researchers used many compounds, for example, 2-Chloro-5-(trifluoromethyl)-4-iodopyridine (cas: 505084-55-9Name: 2-Chloro-5-(trifluoromethyl)-4-iodopyridine).

2-Chloro-5-(trifluoromethyl)-4-iodopyridine (cas: 505084-55-9) 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. 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.Name: 2-Chloro-5-(trifluoromethyl)-4-iodopyridine

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