Category: iodides-buliding-blocks

Selective Synthesis of Functionalized Trifluoromethylated Pyrrolidines, Piperidines, and Azepanes Starting from 1-Tosyl-2-(trifluoromethyl)aziridine was written by Dolfen, Jeroen;Kenis, Sara;Van Hecke, Kristof;De Kimpe, Norbert;D’Hooghe, Matthias. And the article was included in Chemistry – A European Journal in 2014.Name: 1-Chloro-4-iodobutane This article mentions the following:

Substituted trifluoromethyl-substituted aziridines I (R = H, Me, ClCH₂XCH₂CH₂; X = bond, CH₂) were prepared; tandem substitution and cyclization reactions of I (R = ClCH₂XCH₂CH₂; X = bond, CH₂) yielded trifluoromethyl-substituted pyrrolidinemethanamines and piperidinemethanamines II (R¹ = Cl, i-PrNH, i-BuNH, NC, thiocyanato, MeO, EtO; X = bond, CH₂) in 14-98% yields (all but two cases in > 50% yields). Lithiation of I (R = H) [prepared in two steps from F₃CCH(OH)CH₂NH₂] with BuLi in the presence of HMPA at -100° and alkylation with RI (R = Me, ClCH₂XCH₂CH₂; X = bond, CH₂) yielded I (R = Me, ClCH₂XCH₂CH₂; X = bond, CH₂); the presence of an equivalent of HMPA and low temperature were required to obtain the alkylated products. Reaction of I (R = ClCH₂XCH₂CH₂; X = bond, CH₂) with LiCl, isopropyl- and isobutylamines, NaCN, KSCN, and sodium methoxide and ethoxide yielded II (R¹ = Cl, i-PrNH, i-BuNH, NC, thiocyanato, MeO, EtO; X = bond, CH₂); reaction of I [R = (CH₂)₄Cl] with isopropylamine and isobutylamine gave trifluoromethyl azepinemethylamines III (R² = i-Pr, i-Bu) as the major products. The structures of II (R¹ = MeO, EtO; X = bond, CH₂) and III (R² = i-Pr) were determined by X-ray crystallog. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9Name: 1-Chloro-4-iodobutane).

1-Chloro-4-iodobutane (cas: 10297-05-9) 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.Name: 1-Chloro-4-iodobutane

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

Study on mercaptopyridinecarboxylic acids. Part III. Preparation of esters, ethers and ether-esters of mercaptopyridinecarboxylic acids was written by Lejeune, R.;Thunus, L.. And the article was included in Journal de Pharmacie de Belgique in 1980.Quality Control of 5-Iodonicotinic acid This article mentions the following:

Pyridinecarboxylic acids I (R = halo) were treated with thiourea, KSH, and Na₂S-S and the products were converted to the resp. mercapto acids II. Thus, 2-chloro-3-pyridinecarboxylic acid was heated with thiourea, and the product was treated with N₂H₄ to yield the resp. II. II were etherified by MeI and esterified by MeOH and CH₂N₂. In the experiment, the researchers used many compounds, for example, 5-Iodonicotinic acid (cas: 15366-65-1Quality Control of 5-Iodonicotinic acid).

5-Iodonicotinic acid (cas: 15366-65-1) 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. 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 5-Iodonicotinic acid

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

Pd^II-catalyzed monoselective ortho halogenation of C-H bonds assisted by counter cations: a complementary method to directed ortho lithiation was written by Mei, Tian-Sheng;Giri, Ramesh;Maugel, Nathan;Yu, Jin-Quan. And the article was included in Angewandte Chemie, International Edition in 2008.Quality Control of 2-Chloro-6-iodobenzoic acid This article mentions the following:

The yield and selectivity of monoselective ortho halogenation of benzoic acid derivatives were improved greatly by using tetraalkyl ammonium salts as additives. These effects are attributed to the influence of counter cations. The halogenated products are versatile intermediates for the construction of substituted aromatic compounds In the experiment, the researchers used many compounds, for example, 2-Chloro-6-iodobenzoic acid (cas: 13420-63-8Quality Control of 2-Chloro-6-iodobenzoic acid).

2-Chloro-6-iodobenzoic acid (cas: 13420-63-8) 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. 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.Quality Control of 2-Chloro-6-iodobenzoic acid

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

Visible-Light-Enabled Ph₃P/LiI-Promoted Tandem Radical Trifluoromethylation/Cyclization/Iodination of 1,6-Enynes with Togni’s Reagent was written by Liu, Hui;Fan, Xu;Hu, Jinkai;Ma, Tongtong;Wang, Feng;Yang, Jinhui;Li, Dianjun. And the article was included in Journal of Organic Chemistry in 2022.Application of 207115-22-8 This article mentions the following:

The visible-light-induced Ph₃P/LiI-promoted intermol. cascade trifluoromethyl radical addition/5-exo-dig cyclization/iodination of 1,6-enynes R¹CCCH₂XCH₂C(R²)=CH₂ [R¹ = 4-chlorophenyl, thiophen-2-yl, naphthalen-1-yl, etc.; R² = H, Me, Ph, COOEt; X = O, N(Ts), N(Boc)]/2-CCR³C₆H₅-4-R⁴C₆H₃OCH=CH₂ (R³ = H, 4-Me, 3-Cl 4-Br, etc.; R⁴ = H, Me, Br) with Togni’s reagent using LiI as the iodine source without the need of the transition metal, oxidant, and base were reported. This reaction promises to be a useful method for the preparation of trifluoromethyl-substituted and vinyl C-I bond-containing pyrrolidines I and benzofuran products II with good regioselectivity and functional-group tolerance under ambient conditions. 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 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. This periodic order also follows the atomic radius of halogens and the length of the carbon-halogen bond.Application of 207115-22-8

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

Cross-coupling reaction of 2-(1,3-butadienyl)magnesium chloride with alkyl or aryl halides by lithium chloride-cupric chloride (Li₂CuCl₄), a superior catalyst was written by Nunomoto, Sadaaki;Kawakami, Yuhsuke;Yamashita, Yuya. And the article was included in Journal of Organic Chemistry in 1983.Category: iodides-buliding-blocks This article mentions the following:

The combination of lithium chloride-cupric chloride (Li₂CuCl₄) was an excellent catalyst in selective cross-coupling reaction of 2-(1,3-butadienyl)magnesium chloride with alkyl or aryl halides. The order of reactivities for the halides was I > Br > Cl, and alkyl halides > aryl halides and primary halides ≫ secondary halides. N-alkyl bromides and iodides especially exhibited high reactivities in the coupling reactions. In the experiment, the researchers used many compounds, for example, 1-Bromo-4-(2-iodoethyl)benzene (cas: 85356-68-9Category: iodides-buliding-blocks).

1-Bromo-4-(2-iodoethyl)benzene (cas: 85356-68-9) 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. 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

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.Electric Literature of C7H4ClIO2 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-Chloro-2-iodobenzoic acid (cas: 123278-03-5Electric Literature of C7H4ClIO2).

3-Chloro-2-iodobenzoic acid (cas: 123278-03-5) 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 C7H4ClIO2

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

Enantioselective Reductive N-Cyclization-Alkylation Reaction of Alkene-Tethered Oxime Esters and Alkyl Iodides by Nickel Catalysis was written by Jia, Xue-Gong;Yao, Qi-Wei;Shu, Xing-Zhong. And the article was included in Journal of the American Chemical Society in 2022.Application of 85356-68-9 This article mentions the following:

Asym. cross-electrophile difunctionalization of tethered alkenes has become a powerful tool for the production of chiral cyclic scaffolds; however, the current studies all focus on carbocyclization reactions. Herein, an N-cyclization-alkylation reaction and showcase on the potential of heterocyclization for accessing new enantioenriched cyclic architectures is reported. This work establishes a new approach for enantioselective aza-Heck cyclization/cross-coupling sequence, which remains a long-standing unsolved challenge for the synthetic community. The reaction proceeds with primary, secondary, and a few tertiary alkyl iodides, and the use of newly defined ligands gave highly enantioenriched pyrrolines with improved mol. diversity under mild conditions. The presence of imine functionality allows for further structural variations. In the experiment, the researchers used many compounds, for example, 1-Bromo-4-(2-iodoethyl)benzene (cas: 85356-68-9Application of 85356-68-9).

1-Bromo-4-(2-iodoethyl)benzene (cas: 85356-68-9) 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 of 85356-68-9

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

Novel imidazole-based histamine H₃ antagonists was written by Jablonowski, Jill A.;Ly, Kiev S.;Bogenstaetter, Michael;Dvorak, Curt A.;Boggs, Jamin D.;Dvorak, Lisa K.;Lord, Brian;Miller, Kirsten L.;Mazur, Curt;Wilson, Sandy J.;Lovenberg, Timothy W.;Carruthers, Nicholas I.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2009.Quality Control of 1-Chloro-4-iodobutane This article mentions the following:

A novel series of imidazole containing histamine H₃ receptor ligands, i.e. I, were investigated and found to be potent functional antagonists. After improving the stability of these mols. towards liver microsomes, these compounds were found to have no appreciable affinity for CYP P450s. Subsequent in vivo experiments showed significant brain uptake of (4-chloro-phenyl)-[2-(1-isopropyl-piperidin-4-ylmethoxy)-3-methyl-3H-imidazol-4-yl]-methanone I. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9Quality Control of 1-Chloro-4-iodobutane).

1-Chloro-4-iodobutane (cas: 10297-05-9) belongs to iodide derivatives. Iodide-containing intermediates are common in organic synthesis, because of the easy formation and cleavage of the C–I bond. 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.Quality Control of 1-Chloro-4-iodobutane

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

New insights in the structure-activity relationships of 2-phenylamino-substituted benzothiopyrano[4,3-d]pyrimidines as kinase inhibitors was written by Salerno, Silvia;Garcia-Argaez, Aida Nelly;Barresi, Elisabetta;Taliani, Sabrina;Simorini, Francesca;La Motta, Concettina;Amendola, Giorgio;Tomassi, Stefano;Cosconati, Sandro;Novellino, Ettore;Da Settimo, Federico;Marini, Anna Maria;Dalla Via, Lisa. And the article was included in European Journal of Medicinal Chemistry in 2018.Name: 4-Iodo-1,2-dimethoxybenzene This article mentions the following:

Inhibition of angiogenesis via blocking vascular endothelial growth factor receptor (VEGFR) signaling pathway emerged as an established approach in anticancer therapy. So far, many monoclonal antibodies and ATP-competitive small mol. inhibitors have been clin. validated and approved. In this study, structure-activity relationships (SAR) within the 2-phenylamino-substituted benzothiopyrano[4,3-d]pyrimidine class of kinase inhibitors were further refined by the synthesis and biol. evaluation of new compounds 1-21 featuring different substitution patterns on the pendant Ph moiety, combined with H, OCH₃, or Cl at 8-position. Most compounds showed a promising human kinase insert domain receptor (KDR) inhibition profile, with IC₅₀ values in the submicromolar/low nanomolar range, and promising antiproliferative activity on human umbilical vein endothelial cells (HUVECs) as well as on a panel of three human tumor cell lines. The angio-kinase selectivity profile was assessed for the most promising compound 16 against a set of six human kinases. Finally, computational studies allowed clarifying at mol. level the interaction pattern established by the compounds with KDR, highlighting key stable cation-π interactions, and thus providing the basis for further designing novel inhibitors. 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. 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.Name: 4-Iodo-1,2-dimethoxybenzene

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

Nickel-Catalyzed Asymmetric Reductive 1,2-Carboamination of Unactivated Alkenes was written by He, Jun;Xue, Yuhang;Han, Bo;Zhang, Chunzhu;Wang, You;Zhu, Shaolin. And the article was included in Angewandte Chemie, International Edition in 2020.Category: iodides-buliding-blocks This article mentions the following:

Starting from diverse alkene-tethered aryl iodides and O-benzoyl-hydroxylamines, the enantioselective reductive cross-electrophilic 1,2-carboamination of unactivated alkenes was achieved using a chiral pyrox/nickel complex as the catalyst. This mild, modular, and practical protocol provides rapid access to a variety of β-chiral amines with an enantioenriched aryl-substituted quaternary carbon center in good yields and with excellent enantioselectivities. This process reveals a complementary regioselectivity when compared to Pd and Cu catalysis. In the experiment, the researchers used many compounds, for example, (5-Fluoro-2-iodophenyl)methanol (cas: 877264-43-2Category: iodides-buliding-blocks).

(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. 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