Category: iodides-buliding-blocks

A mild approach for the synthesis of indoles from N-(2-iodo-aryl)formamides and phenylacetylene by a copper(I)- and palladium-catalyzed cascade process was written by Ahmed, Atiur;Ghosh, Munmun;Dhara, Shubhendu;Ray, Jayanta K.. And the article was included in Synlett in 2014.Computed Properties of C6H4Cl2IN This article mentions the following:

An efficient one-pot synthesis of phenyl-indoles I [R = 5-CH₃, 5,6-Cl₂, 5-Br, 5-F, etc.] via copper and palladium catalyzed cascade reaction of iodophenylformamide and phenylacetylene in DMF is described. The cascade reaction comprises a Sonogashira cross-coupling, an intramol. CN bond formation, and hydrolysis of the intermediate indole-1-carbaldehyde promoted by the same catalyst and base systems. This methodol. offers several significant advantages such as mild reaction conditions, overall high yields, easy functionalization and operational simplicity. In the experiment, the researchers used many compounds, for example, 4,5-Dichloro-2-iodoaniline (cas: 220185-63-7Computed Properties of C6H4Cl2IN).

4,5-Dichloro-2-iodoaniline (cas: 220185-63-7) belongs to iodide derivatives. Iodide-containing intermediates are common in organic synthesis, because of the easy formation and cleavage of the C–I bond. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.Computed Properties of C6H4Cl2IN

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

Ni-Catalyzed Regioselective Dicarbofunctionalization of Unactivated Olefins by Tandem Cyclization/Cross-Coupling and Application to the Concise Synthesis of Lignan Natural Products was written by KC, Shekhar;Basnet, Prakash;Thapa, Surendra;Shrestha, Bijay;Giri, Ramesh. And the article was included in Journal of Organic Chemistry in 2018.Synthetic Route of C8H9IO2 This article mentions the following:

We disclose a (terpy)NiBr₂-catalyzed reaction protocol that regioselectively difunctionalizes unactivated olefins with tethered alkyl halides and arylzinc reagents. The reaction shows an excellent functional group tolerance (such as ketones, esters, nitriles, and halides) and a moderate to good level of diastereoselectivity. The current cyclization/cross-coupling also tolerates mols. containing base-sensitive racemizable stereocenters, which are preserved without racemization during the reaction. This cyclization/cross-coupling provides a rapid access to (arylmethyl)carbo- and heterocyclic scaffolds, which occur widely as structural cores in various natural products and bioactive mols. In order to show synthetic utility and generality, we have applied this new method in gram-scale quantities to the concise synthesis of six lignan natural products containing three different structural frameworks. We further conducted mechanistic studies with radical probes and selectivity studies, which indicated that the current reaction proceeds via a single electron transfer (SET) process. 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 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. This periodic order also follows the atomic radius of halogens and the length of the carbon-halogen bond.Synthetic Route of C8H9IO2

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

Diasteroselective Synthesis of New Spiropiperidine Scaffolds from the CN(R,S) Building Block was written by Roulland, Emmanuel;Cecchin, Fabrice;Husson, Henri-Philippe. And the article was included in Journal of Organic Chemistry in 2005.Recommanded Product: 10297-05-9 This article mentions the following:

A methodol. allowing the construction of spiropiperidine scaffolds, e.g. I or II, similar to those found in naturally occurring alkaloids was been developed. This approach begins with the well-established CN(R,S) strategy in which the spiro-center was built via intramol. attack of a nitrile function in oxazolopyridinecarbonitriles, e.g. III (n = 1, 2), by an organolithium species obtained by halogen/Li exchange reaction mediated by either t-BuLi or Li naphthalenide. 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. 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.Recommanded Product: 10297-05-9

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

Cyclization via Carbolithiation of α-Amino Alkyllithium Reagents was written by Bahde, Robert J.;Rychnovsky, Scott D.. And the article was included in Organic Letters in 2008.Reference of 10297-05-9 This article mentions the following:

We report a new route to tertiary α-amino stereocenters by sequential alkylation of α-amino nitriles followed by reductive lithiation of the nitrile and cyclization onto an alkene. Reductive lithiation of α-amino nitriles using lithium 4,4′-di-tert-butylbiphenylide (LiDBB) and subsequent intramol. carbolithiation proceeded with modest to high diastereoselectivity to deliver cyclic or spirocyclic ring systems. The stereoselectivity of these intramol. carbolithiations was examined using d. function calculations to evaluate plausible transition state models. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9Reference of 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. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.Reference of 10297-05-9

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

Mild and efficient oxy-iodination of alkynes and phenols with potassium iodide and tert-butyl hydroperoxide was written by Rajender Reddy, K.;Venkateshwar, M.;Uma Maheswari, C.;Santhosh Kumar, P.. And the article was included in Tetrahedron Letters in 2010.Application of 207115-22-8 This article mentions the following:

An efficient synthesis of 1-iodoalkynes and iodophenols was easily achieved by employing simple KI and TBHP. The reaction does not involve the use of a metal and base combination. A variety of substituted alkynes and phenols were prepared with good to excellent yield. 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. 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.Application of 207115-22-8

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

Palladium-Catalyzed, Norbornene-Mediated, ortho-Amination ipso-Amidation: Sequential C-N Bond Formation was written by Whyte, Andrew;Olson, Maxwell E.;Lautens, Mark. And the article was included in Organic Letters in 2018.COA of Formula: C7H4ClIO2 This article mentions the following:

A palladium-catalyzed, norbornene-mediated ortho- and ipso-C-N bond-forming Catellani reaction is reported. This reaction proceeds through a sequential intermol. amination followed by intramol. cyclization of a tethered amide. The products, ortho-aminated dihydroquinolinones, e.g. I, were generated in moderate to good yields and are present in bioactive mols. This work highlights the challenge of competing intra- vs intermol. palladium-catalyzed processes. In the experiment, the researchers used many compounds, for example, 2-Chloro-6-iodobenzoic acid (cas: 13420-63-8COA of Formula: C7H4ClIO2).

2-Chloro-6-iodobenzoic acid (cas: 13420-63-8) 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. 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: C7H4ClIO2

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

Catalytic functionalization of unactivated primary C-H bonds directed by an alcohol was written by Simmons, Eric M.;Hartwig, John F.. And the article was included in Nature (London, United Kingdom) in 2012.Application In Synthesis of N,N-Diethyl-4-iodobenzamide This article mentions the following:

New synthetic methods for the catalytic functionalization of C-H bonds have the potential to revolutionize the synthesis of complex mols. However, the realization of this synthetic potential requires the ability to functionalize selectively one C-H bond in a compound containing many such bonds and an array of functional groups. The site-selective functionalization of aliphatic C-H bonds is one of the greatest challenges that must be met for C-H bond functionalization to be used widely in complex-mol. synthesis, and processes catalyzed by transition-metals provide the opportunity to control selectivity. Current methods for catalytic, aliphatic C-H bond functionalization typically rely on the presence of one inherently reactive C-H bond, or on installation and subsequent removal of directing groups that are not components of the desired mol. To overcome these limitations, we sought catalysts and reagents that would facilitate aliphatic C-H bond functionalization at a single site, with chemoselectivity derived from the properties of the catalyst and site-selectivity directed by common functional groups contained in both the reactant and the desired product. Here, we show that the combination of an iridium-phenanthroline catalyst and a dihydridosilane reagent leads to the site-selective γ-functionalization of primary C-H bonds controlled by a hydroxyl group, the most common functional group in natural products. The scope of the reaction encompasses alcs. and ketones bearing many substitution patterns and auxiliary functional groups; this broad scope suggests that this methodol. will be suitable for the site-selective and diastereoselective functionalization of complex natural products. For example, treating (+)-fenchol with [Ir(cod)OMe]₂ and Et₂SiH gave the corresponding diethyl(hydrido)silyl ether, which was cyclized using [Ir(cod)OMe]₂/Me₄phen to give an intermediate oxasiloxane. The latter compound was oxidized under Tamao-Fleming conditions and then diacylated to give hydroxyfenchol diacetate I in 66% yield. In the experiment, the researchers used many compounds, for example, N,N-Diethyl-4-iodobenzamide (cas: 77350-52-8Application In Synthesis of N,N-Diethyl-4-iodobenzamide).

N,N-Diethyl-4-iodobenzamide (cas: 77350-52-8) 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.Application In Synthesis of N,N-Diethyl-4-iodobenzamide

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

Salt-Templated Solvothermal Synthesis of Dioxane-Linked Three-Dimensional Nanoporous Organic Polymers for Carbon Dioxide and Iodine Capture was written by Ashirov, Timur;Song, Kyung Seob;Coskun, Ali. And the article was included in ACS Applied Nano Materials.Name: 4-Iodo-1,2-dimethoxybenzene This article mentions the following:

Precise control over the textural properties of porous organic polymers, POPs, is a daunting task, yet highly important to achieve desired porosity and pore connectivity for the target applications. Accordingly, the introduction of hard templates in the solvothermal synthesis of POPs could help to control the surface area and pore size without altering their chem. structure. In this direction, here, we synthesized a dioxane linked 3D tetraphenylene-based nanoporous organic polymer (3D-tPOP) using low-cost and readily available NaCl salt as a hard template under solvothermal conditions. The presence of hard template enhanced the surface area and enabled control over the morphol., micropore/mesopore ratio as well as the pore volume with respect to the template amount Whereas micron-sized NaCl templates facilitated the surface growth of a microporous polymer network, nanosized NaCl crystallites led to formation of mesopores. The resulting 3D-tPOPs showed tunable micropore/mesopore ratios and surface areas in the range of 349 to 1058 m² g^-1 with a linear correlation to the template amount High CO₂ uptake capacity of 5.02 mmol g^-1 at 273 K, 1 bar and iodine uptake capacity of 1180 mg g^-1 were observed for 3D-tPOPs with micropore and mesopore ratios of 50.2% and 71.4%, resp. In the experiment, the researchers used many compounds, for example, 4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2Name: 4-Iodo-1,2-dimethoxybenzene).

4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2) 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.Name: 4-Iodo-1,2-dimethoxybenzene

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

Photochemistry of heterocyclic compounds. VII. Photochemical reaction of 2,5-diphenyl-1,3,4-oxadiazole with benzo[b]thiophenes was written by Oe, Koji;Tashiro, Masashi;Tsuge, Otohiko. And the article was included in Bulletin of the Chemical Society of Japan in 1977.Related Products of 36748-88-6 This article mentions the following:

Irradiation of 2,5-diphenyloxadiazole (I) with benzothiophene II (R = H) gives 3-benzoylbenzothiophene III (R¹ = PhCO), its benzoylhydrazone [III; R¹ = PhC(:NNHCOPh)], and/or the oxadiazepine IV; the yields depend on the nature of solvents. With Ph₂CO as a sensitizer, the photochem. reaction of I with II (R = H) forms the [2+2] cycloadduct V. IV is photochem. dissociated to I and II (R = H). In the case of 2-methylbenzothiophene VI, 3-benzoyl-2-methylbenzothiophene benzoylhydrazone is formed, and with Ph₂CO as a sensitizer the [2+2] cycloadduct II (R = Me) is obtained. In the absence or presence of Ph₂CO, however, irradiation of I with 3-methylbenzothiophene gives the [2+2] cycloadduct VII. The photochem. reaction of I with II (R = H, Me) in the presence of iodine gives the corresponding 3-benzoylbenzothiophene and benzoylhydrazone, resp. In the case of 3-methylbenzothiophene, however, the [2+2] cycloadduct VIII is formed, together with 2-benzoyl-3-methylbenzothiophene. In the experiment, the researchers used many compounds, for example, 3-Iodobenzo[b]thiophene (cas: 36748-88-6Related Products of 36748-88-6).

3-Iodobenzo[b]thiophene (cas: 36748-88-6) 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. This periodic order also follows the atomic radius of halogens and the length of the carbon-halogen bond.Related Products of 36748-88-6

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

Pd-Catalyzed Asymmetric Three-Component Allenol Carbopalladation and Allylic Cycloaddition Cascade: A Route to Functionalized Tetrahydrofurans was written by Li, Hongfang;Khan, Ijaz;Li, Qun;Zhang, Yong Jian. And the article was included in Organic Letters in 2022.Recommanded Product: 4-Iodo-1,2-dimethoxybenzene This article mentions the following:

The first Pd-catalyzed asym. three-component reaction of 2,3-allenol, aryl iodides RI (R = 4-methoxyphenyl, 2H-1,3-benzodioxol-5-yl, thiophen-2-yl, etc.) and 2-arylmethylenemalononitriles R¹CH=C(CN)₂ (R¹ = 2-methylphenyl, 2H-1,3-benzodioxol-5-yl, furan-2-yl, etc.) has been developed via an allenol carbopalladation and an allylic cycloaddition cascade. This process allows rapid access to substituted tetrahydrofurans I bearing diverse functional groups in good yields with high diastereoselectivities and excellent enantioselectivities. The concise total synthesis of a lignan, (-)-2-episesaminone, has been achieved by the elaboration of a functionalized THF obtained from this reaction. 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. 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.Recommanded Product: 4-Iodo-1,2-dimethoxybenzene

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