Tag: 300-400

Functional Group Tolerant Kumada-Corriu-Tamao Coupling of Nonactivated Alkyl Halides with Aryl and Heteroaryl Nucleophiles: Catalysis by a Nickel Pincer Complex Permits the Coupling of Functionalized Grignard Reagents was written by Vechorkin, Oleg;Proust, Valerie;Hu, Xile. And the article was included in Journal of the American Chemical Society in 2009.Application In Synthesis of N,N-Diethyl-4-iodobenzamide This article mentions the following:

A nickel(II) pincer complex [(^MeNN₂)NiCl] (I) [^MeNN₂ = di(2-dimethylaminophenyl)amine] catalyzes Kumada-Corriu-Tamao cross-coupling of nonactivated alkyl halides with aryl and heteroaryl Grignard reagents. The coupling of octyl bromide with phenylmagnesium chloride was used as a test reaction. Using 3 mol % of I as the precatalyst and THF as the solvent, and in the presence of a catalytic amount of TMEDA, the coupling product was obtained in a high yield. The reaction conditions could be applied to cross coupling of other primary and secondary alkyl bromides and iodides. The coupling is tolerant to a wide range of functional groups. Therefore, alkyl halides containing ester, amide, ether, thioether, alc., pyrrole, indole, furan, nitrile, conjugated enone, and aryl halide moieties were coupled to give high isolated yields of products in which these units stay intact. For the coupling of ester-containing substrates, O-TMEDA is a better additive than TMEDA. The reaction protocol proves to be efficient for the coupling of Knochel-type functionalized Grignard reagents. Thus, aryl Grignard reagents containing electron-deficient and/or sensitive ester, nitrile, amide, and CF₃ substituents could be successfully coupled to nonactivated and functionalized alkyl iodides. The catalysis is also efficient for the coupling of alkyl iodides with functionalized heteroaryl Grignard reagents, giving rise to pyridine-, thiophene-, pyrazole-, furan-containing mols. with addnl. functionalities. Concerning the mechanism of the catalysis, [(^MeNN₂)Ni-(hetero)Ar] was identified as an intermediate, and the activation of alkyl halides was found to take place through a radical-rebound process. 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. 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 In Synthesis of N,N-Diethyl-4-iodobenzamide

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

Modular synthesis of helicene-like compounds based on the imidazolium motif was written by Cizkova, Martina;Saman, David;Koval, Dusan;Kasicka, Vaclav;Klepetarova, Blanka;Cisarova, Ivana;Teply, Filip. And the article was included in European Journal of Organic Chemistry in 2014.Synthetic Route of C3H2I2N2 This article mentions the following:

Straightforward synthesis of novel mono- and tricationic helical compounds based on the imidazolium core was developed. The synthetic route based on double [2+2+2] cycloaddition reactions of precursors with the imidazolium core motif is notably modular and reaches beyond established protocols used for the synthesis of imidazolium systems as well as beyond the reported protocols used to assemble compounds with helical frameworks. This approach opened rapid four-step access to a cationic species featuring nine ortho-annulated rings that represents the highest order helical nitrogen-based cationic system reported to date. The structure of 2 was confirmed by the single crystal x-ray diffraction anal. [monoclinic, space group C2/c, a 39.389(3), b 14.2400(12), c 17.8968(14) Å, β 114.276(3)°, V 9150.7(13) ų, Z 8]. The detailed crystallog. data were deposited at the Cambridge Crystallog. Data Center as supplementary publication number CCDC 955735. In the experiment, the researchers used many compounds, for example, 4,5-Diiodo-1H-imidazole (cas: 15813-09-9Synthetic Route of C3H2I2N2).

4,5-Diiodo-1H-imidazole (cas: 15813-09-9) belongs to iodide derivatives. 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.Synthetic Route of C3H2I2N2

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

The direct iodination of polyalkylbenzenes bearing bulky groups was written by Suzuki, Hitomi;Nakamura, Kiyomi;Goto, Ryozo. And the article was included in Bulletin of the Chemical Society of Japan in 1966.COA of Formula: C10H12I2 This article mentions the following:

A number of polyalkylbenzenes, bearing bulky substituents, afforded mono-iodo derivatives in high yield when treated with iodine-HIO₄. HIO₄ proved to be the most effective of several oxidizing agents examnd.: Ag₂SO₄, AgClO₄, HgO, K₂S₂O₈, HIO₃, and ο-IC₆H₄OMe. The reaction also proceded smoothly to yield mono- and diiodo derivatives of some polymethylbenzenes, but tri- and tetraiodination of xylene was difficult to effect. In a typical preparation a mixture of 5.40 g. 5-tert-Bu-1,3-Me₂C₆H₃, 1.54 g. HIO₄.2H₂O, 3.39 g. iodine, and 20 ml. 10:2:0.3 AcOH-H₂O-H₂SO₄ was stirred 4 hrs. at 60-5°. The mixture was cooled and the solid product was crystallized from petr. ether to give 8.7 g. 4-tert-Bu-2,6-Me₂C₆H₂I, m. 59-60°. The iodine atom was assumed to enter the ring para to the tert-Bu group. A similar procedure afforded the following compounds in good yield (compound, reaction time, reaction temperature, m.p., and b.p./mm. given): 5-tert-Bu-2,3-Me₂C₆H₂I, 6-7 hrs., 60-5°,–, 146-7°/14; 6-tert-Bu-2,3,4-Me₃C₆HI, 6-7 hrs., 60-5°, 74-5°,–; 2,3,5,6-iso-Pr₄C₆HI, 30 hrs., 75-80°, 161-3°,–; 2,5-tert-Bu₂C₆H₃I, ∼30 hrs., 75-80°,–, 156-7°/13-14; 4,5-I₂-1,2-Me₂C₆H₂, 3-4 hrs., 70°, 93-4°,–; 2,5-I₂-1,4-Me₂C₆H₂, 3-4 hrs., 70°, 104-5°,–; diiodoprehnitene, 1.5 hrs., 70°, 190-1°,–; diiododurene, 1.5 hrs., 70°, 140-1°,–. Where necessary, compounds were purified by chromatography over alumina and structures were verified by ir spectral examination In the experiment, the researchers used many compounds, for example, 1,4-Diiodo-2,3,5,6-tetramethylbenzene (cas: 3268-21-1COA of Formula: C10H12I2).

1,4-Diiodo-2,3,5,6-tetramethylbenzene (cas: 3268-21-1) 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.COA of Formula: C10H12I2

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

Preparation and Diels-Alder Chemistry of 4-Vinylimidazoles was written by Lovely, Carl J.;Du, Hongwang;Rasapalli, Sivappa;Bhandari, Manojkumar R.;He, Yong;Dias, H. V. Rasika. And the article was included in Journal of Organic Chemistry in 2007.Category: iodides-buliding-blocks This article mentions the following:

Various 4-vinylimidazole derivatives have been prepared from the corresponding 4-iodoimidazoles or from urocanic acid. Several methods for the elaboration of these vinylimidazoles and their Diels-Alder reactions are reported. All of the vinylimidazoles prepared in the course of this study react with N-phenylmaleimide quite readily with mild thermal activation providing a single cycloadduct, in most cases the initial, nonaromatic adduct. With more electron rich substrates, there is a tendency for these initial cycloadducts to undergo aromatization, ene reaction, and oxidation although this can be circumvented to a large extent by the choice of reaction conditions. Limited reactions were observed with other dienophiles, providing the expected cycloadducts in most cases, although an abnormal adduct was obtained in one case with di-Me acetylene dicarboxylate. These substrates also participate in regioselective Diels-Alder reactions with monoactivated dienophiles, but require fairly forcing conditions, thus only providing the aromatized cycloadducts in modest yields. An investigation of substituent effects at the 2-position of the imidazole moiety was undertaken, in which electron-donating and weakly electron-withdrawing substituents are tolerated. In addition, several substrates with terminally substituted vinyl moieties have been investigated. In the experiment, the researchers used many compounds, for example, 4,5-Diiodo-1H-imidazole (cas: 15813-09-9Category: iodides-buliding-blocks).

4,5-Diiodo-1H-imidazole (cas: 15813-09-9) 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. 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

The reactivity of 2-fluoro- and 2-chloropyridines toward sodium ethoxide: Factors governing the rates of nucleophilic (het)aromatic substitutions was written by Schlosser, Manfred;Rausis, Thierry. And the article was included in Helvetica Chimica Acta in 2005.Electric Literature of C6H2ClF3IN This article mentions the following:

The relative displacement rates of the halide substituent from 2-fluoro- and 2-chloropyridines by EtONa in EtOH at +25° were assessed by competition kinetics. The 2-fluoropyridine reacts 320 times faster than the chloro analog. A CF₃ group increases the reactivity more than single halogen atoms do, whatever the element, and the latter are superior to Me₃Si groups. Substituents accommodated at the 4-position operate through their inductive effect, whereas at the 3-position, this action may be attenuated by steric hindrance. Almost all 5-substituents enhance the rate of the nucleophilic substitution occurring at the 2-position. The sole exception concerns the F-atom at the 5-position which retards the reaction, presumably by lone-pair/lone-pair repulsion with the neg. charge building up at the central C-atom of the intermediate Meisenheimer complex. The substituent effects are additive. Therefore, by using the increments derived from the present work, the rates of future reactions should be predictable with fair accuracy. In the experiment, the researchers used many compounds, for example, 2-Chloro-5-(trifluoromethyl)-4-iodopyridine (cas: 505084-55-9Electric Literature of C6H2ClF3IN).

2-Chloro-5-(trifluoromethyl)-4-iodopyridine (cas: 505084-55-9) 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.Electric Literature of C6H2ClF3IN

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

From supramolecular porphyrin tweezers to dynamic A_nB_mC_lD_k multiporphyrin arrangements through orthogonal coordination was written by Kishore, Ravuri S. K.;Paululat, Thomas;Schmittel, Michael. And the article was included in Chemistry – A European Journal in 2006.Product Details of 3268-21-1 This article mentions the following:

A dynamic, supramol., three-component A_nB_mC₁ bis(zinc porphyrin) tweezer,containing Cu(I), I (R = 2,4,6-trimethylphenyl, R¹ = 4-bromo-2,3,5,6-tetramethylphenyl), and II (R² = dodecyl) was prepared quant. using the heteroleptic bisphenanthroline (HETPHEN) concept. Upon addition of nitrogenous spacers of different length, namely, the extended 1,4-bis(4′-pyridylethynyl)durene (3a), 4,4′-bipyridine (3b), and 1,4-diazabicyclo[2.2.2]octane (DABCO; 3c), to set up an addnl. orthogonal binding motif (Zn_Por-N_spacer), three structurally different, still dynamic, four-component A_nB_mC₁D_k assemblies were cleanly formed, as indicated by UV/visible and NMR titrations as well as by DOSY studies. The structures were identified as a bridged monotweezer A₂BC₂D, a doubly bridged double tweezer A₄B₂C₄D₂, and a triply bridged double tweezer A₄B₂C₄D₃, the latter resembling a porphyrin stack. Notably, the same structures were equally formed directly from a mixture of the constituents A, B, C, and D put together in any sequence if the correct stoichiometry was applied. In the experiment, the researchers used many compounds, for example, 1,4-Diiodo-2,3,5,6-tetramethylbenzene (cas: 3268-21-1Product Details of 3268-21-1).

1,4-Diiodo-2,3,5,6-tetramethylbenzene (cas: 3268-21-1) 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. 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 3268-21-1

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

m-Iodosylbenzoic acid – a convenient recyclable reagent for highly efficient aromatic iodinations was written by Kirschning, Andreas;Yusubov, Mekhman S.;Yusubova, Roza Y.;Chi, Ki-Whan;Park, Joo Y.. And the article was included in Beilstein Journal of Organic Chemistry in 2007.Category: iodides-buliding-blocks This article mentions the following:

M-Iodosylbenzoic acid is used to perform iodination of arenes in the presence of iodine at room temperature in acetonitrile. Separation of pure products is conveniently achieved by scavenging any aryl iodide by ion exchange with IRA-900 (hydroxide form). The reduced form of the reagent, m-iodobenzoic acid, can be easily recovered from the ion exchange resin or from the basic aqueous solution by simple acidification with HCl. In the experiment, the researchers used many compounds, for example, 4,5-Diiodo-1H-imidazole (cas: 15813-09-9Category: iodides-buliding-blocks).

4,5-Diiodo-1H-imidazole (cas: 15813-09-9) belongs to iodide derivatives. Iodide-containing intermediates are common in organic synthesis, because of the easy formation and cleavage of the C–I bond. 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.Category: iodides-buliding-blocks

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

Bergman cycloaromatization of imidazole-fused enediynes: the remarkable effect of N-aryl substitution was written by Zhao, Zhengrong;Peng, Yunshan;Dalley, N. Kent;Cannon, John F.;Peterson, Matt A.. And the article was included in Tetrahedron Letters in 2004.Recommanded Product: 4,5-Diiodo-1H-imidazole This article mentions the following:

A series of N-aryl-substituted ‘imidazole-fused’ (Z) 3-ene-1,5-diynes, e.g., I, was prepared and kinetic parameters for their Bergman cycloaromatization reactivities were determined N-Arylation enhanced rates relative to N-alkyl derivatives by up to sevenfold (ANOVA p<0.0001). The greatest enhancement was exhibited by I. In the experiment, the researchers used many compounds, for example, 4,5-Diiodo-1H-imidazole (cas: 15813-09-9Recommanded Product: 4,5-Diiodo-1H-imidazole).

4,5-Diiodo-1H-imidazole (cas: 15813-09-9) 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.Recommanded Product: 4,5-Diiodo-1H-imidazole

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

Ir^III-Catalyzed Selective ortho-Monoiodination of Benzoic Acids with Unbiased C-H Bonds was written by Weis, Erik;Johansson, Magnus J.;Martin-Matute, Belen. And the article was included in Chemistry – A European Journal in 2020.COA of Formula: C7H4BrIO2 This article mentions the following:

An iridium-catalyzed selective ortho-monoiodination of benzoic acids with two equivalent C-H bonds was presented. A wide range of electron-rich and electron-poor substrates underwent the reaction under mild conditions, with >20:1 mono/di selectivity. Importantly, the C-H iodination occurred selectively ortho to the carboxylic acid moiety in substrates bearing competing coordinating directing groups. The reaction was performed at room temperature and no inert atm. or exclusion of moisture was required. Mechanistic investigations revealed a substrate-dependent reversible C-H activation/protodemetalation step, a substrate-dependent turnover-limiting step and the crucial role of the AgI additive in the deactivation of the iodination product towards further reaction. In the experiment, the researchers used many compounds, for example, 3-Bromo-2-iodobenzoic acid (cas: 503821-94-1COA of Formula: C7H4BrIO2).

3-Bromo-2-iodobenzoic acid (cas: 503821-94-1) 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.COA of Formula: C7H4BrIO2

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

Copper-Catalyzed Cross-Coupling of Functionalized Alkyl Halides and Tosylates with Secondary and Tertiary Alkyl Grignard Reagents was written by Ren, Peng;Stern, Lucas-Alexandre;Hu, Xile. And the article was included in Angewandte Chemie, International Edition in 2012.Application In Synthesis of 1-Bromo-4-(2-iodoethyl)benzene This article mentions the following:

A highly efficient method for the cross-coupling of non-activated and functionalized alkyl halides and tosylates with secondary and tertiary alkyl Grignard reagents has been developed. The copper-based method is remarkably practical and general. The wide scope, and especially the tolerance to a large number of important yet sensitive functional groups, make this method attractive for the streamlined synthesis of functional mols. In the experiment, the researchers used many compounds, for example, 1-Bromo-4-(2-iodoethyl)benzene (cas: 85356-68-9Application In Synthesis of 1-Bromo-4-(2-iodoethyl)benzene).

1-Bromo-4-(2-iodoethyl)benzene (cas: 85356-68-9) 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. This periodic order also follows the atomic radius of halogens and the length of the carbon-halogen bond.Application In Synthesis of 1-Bromo-4-(2-iodoethyl)benzene

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