Tag: 200-300

Mechanistic insight into the synergistic Cu/Pd-catalyzed carbonylation of aryl iodides using alcohols and dioxygen as the carbonyl source was written by Li, Junxuan;Zhou, Jinlei;Wang, Yumei;Yu, Yue;Liu, Qiang;Yang, Tilong;Chen, Huoji;Cao, Hua. And the article was included in Science China: Chemistry in 2022.Electric Literature of C7H6FIO This article mentions the following:

Pd-catalyzed carbonylation, as an efficient synthetic approach for the installation of carbonyl groups in organic compounds, has been one of the most important research fields in the past decade. Although elegant reactions that allow highly selective carbonylations have been developed, straightforward routes with improved reaction activity and broader substrate scope remain long-term challenges for new practical applications. Here, authors show a new type of synergistic Cu/Pd-catalyzed carbonylation reaction using alcs. and dioxgen as the carbonyl sources. A broad range of aryl iodides and alcs. are compatible with this protocol. The reaction is concise and practical due to the ready availability of the starting materials and the scalability of the reaction. In addition, the reaction affords lactones and lactams in an intermol. fashion. Moreover, DFT calculations have been performed to study the detailed mechanisms. In the experiment, the researchers used many compounds, for example, (5-Fluoro-2-iodophenyl)methanol (cas: 877264-43-2Electric Literature of C7H6FIO).

(5-Fluoro-2-iodophenyl)methanol (cas: 877264-43-2) 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.Electric Literature of C7H6FIO

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

Synthesis of Enantiopure Bicyclic α,α-Disubstituted Spirolactams via Asymmetric Birch Reductive Alkylation was written by Gueret, Stephanie M.;O’Connor, Patrick D.;Brimble, Margaret A.. And the article was included in Organic Letters in 2009.Name: 1-Chloro-4-iodobutane This article mentions the following:

The synthesis of enantiopure bicyclic α,α-disubstituted spirolactams is described using a diastereoselective Birch reductive alkylation as the key step. Hydrogenation of the resultant alkylated cyclohexadienes followed by intramol. cyclization provides access to enantiopure 8-azaspiro[5.6]dodecan-7-ones, e.g. I. 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. 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.Name: 1-Chloro-4-iodobutane

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

Accessing 2-Arylbenzofurans by Cu^I₂(pip)₂-Catalyzed Tandem Coupling/Cyclization Reaction: Mechanistic Studies and Application to the Synthesis of Stemofuran A and Moracin M was written by Chen, Hong-Bin;Qin, Dan-Dan;Chen, Wei;Tang, Xiao;Yu, Wen;Wu, An-An;Liao, Yi. And the article was included in Asian Journal of Organic Chemistry in 2016.Product Details of 207115-22-8 This article mentions the following:

An asym. dinuclear copper(I) complex, Cu^I2(pip)₂ (pip = (2-picolyliminomethyl)pyrrole anion), was utilized to catalyze the tandem coupling/cyclization reaction of o-iodophenols and terminal alkynes, which led to the formation of valuable 2-arylbenzofurans I (R¹ = Ph, 4-EtC₆H₄, 1-naphthyl, etc.; R² = H, 4-MeO, 4-t-Bu, 4-Ph, 4-F, 4-Br) in good yields. DFT calculations showed that the two proximate copper atoms play cooperative roles throughout the catalytic cycle. Using this catalytic protocol, bioactive natural products stemofuran A and moracin M were concisely synthesized. In the experiment, the researchers used many compounds, for example, 4-Bromo-2-iodophenol (cas: 207115-22-8Product Details of 207115-22-8).

4-Bromo-2-iodophenol (cas: 207115-22-8) 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. This periodic order also follows the atomic radius of halogens and the length of the carbon-halogen bond.Product Details of 207115-22-8

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

The synthesis of substituted 9-oxoacridan-4-carboxylic acids; part 3. The reaction of methyl anthranilates with diphenyliodonium-2-carboxylates was written by Rewcastle, Gordon W.;Denny, William A.. And the article was included in Synthesis in 1985.SDS of cas: 13420-63-8 This article mentions the following:

Twenty-two 9-oxoacridan-4-carboxylic acids I (R = H, 1-Me, 1-OMe, 1-Cl, 1-NO₂, 1-CO₂H, 2-Me, 3-Me, etc., R¹ = H, R = H, R¹ = 6-NH₂, 6-Cl, 6-NO₂, 7-NO₂, 8-Me, 8-Cl) were prepared by cyclization of anilinobenzoates II followed by saponification II were prepared by treating diphenyliodonium-2-carboxylates III with Me anthranilates IV. In the experiment, the researchers used many compounds, for example, 2-Chloro-6-iodobenzoic acid (cas: 13420-63-8SDS of cas: 13420-63-8).

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

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

adj-Dicarbaporphyrinoid Systems: Synthesis, Spectroscopic Characterization, and Reactivity of 23-Carbabenziporphyrins was written by Jain, Pankaj;AbuSalim, Deyaa I.;Lash, Timothy D.. And the article was included in Journal of Organic Chemistry in 2019.Safety of 3-Iodo-4-methoxybenzaldehyde This article mentions the following:

A new family of adj-dicarbaporphyrinoids has been prepared using the “2 + 2” MacDonald methodol. Dibutylboron triflate catalyzed condensation of 3-iodo-4-methoxybenzaldehyde with an indene enamine afforded an iodofulvene aldehyde; and a related dimethoxyfulvene was similarly prepared in two steps from 2,4-dimethoxybenzaldehyde. Following protection as the corresponding di-Me acetals, the iodofulvenes were metalated with Bu₃MgLi at -100 °C and reacted with DMF to give the required fulvene dialdehyde intermediates. Acid-catalyzed condensation with three different dipyrrylmethanes afforded a series of benzo-23-carbabenziporphyrins I (R = Et, Me, CH₂CH₂CO₂Me, X = H; R = Et, Me, CH₂CH₂CO₂Me, X = OMe) in 52-70% yields. The proton NMR spectra for these adj-dicarbaporphyrinoids indicate that these macrocycles are slightly diatropic. Monoprotonation afforded cationic species with slightly larger aromatic ring currents, and under strongly acidic conditions, C-protonated dications were generated with substantial diatropic properties. The aromatic character of these structures was supported by nucleus-independent chem. shifts and anisotropy of induced c.d. calculations The computational results indicate that the dications favor 23-atom 22π electron delocalization pathways. The benzo-23-carbabenziporphyrins were selectively oxidized with silver(I) acetate in dichloromethane-methanol to give stable nonaromatic structures with two addnl. methoxy substituents connected to sp³ hybridized bridging carbons. The intriguing reactivity and unique spectroscopic properties of benzo-23-carbabenziporphyrins make these novel structures promising candidates for further investigations. In the experiment, the researchers used many compounds, for example, 3-Iodo-4-methoxybenzaldehyde (cas: 2314-37-6Safety of 3-Iodo-4-methoxybenzaldehyde).

3-Iodo-4-methoxybenzaldehyde (cas: 2314-37-6) 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. 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.Safety of 3-Iodo-4-methoxybenzaldehyde

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

Palladium-Catalyzed Regioselective Carbonylative Coupling/Amination of Aryl Iodides with Unactivated Alkenes: Efficient Synthesis of β-Aminoketones was written by Peng, Jin-Bao;Wu, Fu-Peng;Li, Da;Geng, Hui-Qing;Qi, Xinxin;Ying, Jun;Wu, Xiao-Feng. And the article was included in ACS Catalysis in 2019.Recommanded Product: 5460-32-2 This article mentions the following:

The carbonylative coupling of aryl halides with unactivated alkenes remains a challenge, because of the low reactivity of acyl-palladium intermediate to the olefins. A palladium-catalyzed carbonylative coupling/amination of aryl iodides with unactivated alkenes for the synthesis of β-aminoketone derivatives was developed. With the assistance of a directing group (8-aminoquinoline, AQ), the coordination of the olefin to acyl-palladium complex can be enhanced, thereby promoting the acylpalladation across the C:C double bonds. A broad range of β-aminoketone derivatives were prepared in moderate to excellent yields with complete regioselectivity by using 4-pentenoic and 2-vinylbenzoic amide derivatives as the starting materials. This methodol. involves the formation of two C-C bonds as well as one C-N bond, and provided a method for the carbonylative difunctionalization of unactivated alkenes. In the experiment, the researchers used many compounds, for example, 4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2Recommanded Product: 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. 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: 5460-32-2

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

Synthesis of new bis[heterocycles] by a one-pot Sonogashira coupling reaction was written by Deodhar, Mandar;Black, David StC;Kumar, Naresh. And the article was included in Heterocycles in 2011.Computed Properties of C8H7IO2 This article mentions the following:

Halogenated flavones, isoflavones and indoles were subjected to a one-pot Sonogashira coupling reaction and the synthesis of the target compounds was achieved in good yield. For example, iodination and Sonogashira coupling of Daidzein diacetate [7-(acetyloxy)-3-[4-(acetyloxy)phenyl]-4H-1-benzopyran-4-one] with (trimethylsilyl)acetylene thus provided 2,1-ethynediyl(methoxy-4,1-phenylene)bis[7-methoxy-4H-1-benzopyran-4-one]. The methodol. can be readily adapted to the synthesis of a wide variety of substituted bis[heterocyclic compounds]. In the experiment, the researchers used many compounds, for example, 3-Iodo-4-methoxybenzaldehyde (cas: 2314-37-6Computed Properties of C8H7IO2).

3-Iodo-4-methoxybenzaldehyde (cas: 2314-37-6) belongs to iodide derivatives. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.Computed Properties of C8H7IO2

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

Ligand-Enabled β-C-H Arylation of α-Amino Acids Using a Simple and Practical Auxiliary was written by Chen, Gang;Shigenari, Toshihiko;Jain, Pankaj;Zhang, Zhipeng;Jin, Zhong;He, Jian;Li, Suhua;Mapelli, Claudio;Miller, Michael M.;Poss, Michael A.;Scola, Paul M.;Yeung, Kap-Sun;Yu, Jin-Quan. And the article was included in Journal of the American Chemical Society in 2015.Synthetic Route of C8H9IO2 This article mentions the following:

Palladium-catalyzed β-C-H functionalizations of carboxylic acid derivatives using an auxiliary as a directing group have been extensively explored in the past decade. In comparison to the most widely used auxiliaries in asym. synthesis, the simplicity and practicality of the auxiliaries developed for C-H activation remains to be improved. The authors previously developed a simple N-methoxyamide auxiliary to direct β-C-H activation, albeit this system was not compatible with carboxylic acids containing α-hydrogen atoms. Herein, the authors report the development of a pyridine-type ligand that overcomes this limitation of the N-methoxyamide auxiliary, leading to a significant improvement of β-arylation of carboxylic acid derivatives, especially α-amino acids. The arylation using this practical auxiliary is applied to the gram-scale syntheses of unnatural amino acids, bioactive mols., and chiral bis(oxazoline) ligands. 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. 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.Synthetic Route of C8H9IO2

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

Expedient Access to 2,3-Dihydropyridines from Unsaturated Oximes by Rh(III)-Catalyzed C-H Activation was written by Romanov-Michailidis, Fedor;Sedillo, Kassandra F.;Neely, Jamie M.;Rovis, Tomislav. And the article was included in Journal of the American Chemical Society in 2015.Related Products of 10297-05-9 This article mentions the following:

α,β-Unsaturated oxime pivalates are proposed to undergo reversible C(sp²)-H insertion with cationic Rh(III) complexes to furnish five-membered metallacycles. In the presence of 1,1-disubstituted olefins, these species participate in irreversible migratory insertion to give, after reductive elimination, 2,3-dihydropyridine products in good yields. Catalytic hydrogenation can then be used to convert these mols. into piperidines, which are important structural components of numerous pharmaceuticals. Thus, e.g., heterocyclization of unsaturated oxime pivalate I with alkene II in presence of [Rh(MeCN)₃(C₅Me₄CF₃)](SbF₆)₂ afforded dihydropyridine III (99%). In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9Related Products of 10297-05-9).

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. 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.Related Products of 10297-05-9

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

P/N Heteroleptic Cu(I)-Photosensitizer-Catalyzed Deoxygenative Radical Alkylation of Aromatic Alkynes with Alkyl Aldehydes Using Dipropylamine as a Traceless Linker Agent was written by Bao, Hanyang;Zhou, Bingwei;Luo, Shu-Ping;Xu, Zheng;Jin, Hongwei;Liu, Yunkui. And the article was included in ACS Catalysis in 2020.Electric Literature of C8H5IS This article mentions the following:

A deoxygenative radical alkylation of aromatic alkynes with alkyl aldehydes for the preparation of allylarenes was successfully achieved. This transformation is accomplished through the reaction of alkyl aldehydes with alkynes in the presence of dipropylamine and Hantzsch ester catalyzed by a P/N heteroleptic Cu(I)-based photosensitizer under photoredox catalysis conditions. Preliminary mechanistic studies reveal that this aldehyde-alkyne coupling process comprises a regioselective radical addition of in-situ-generated alkyl-substituted α-amino radicals to alkynes with subsequent 1,5-proton transfer, C-N bond cleavage and concomitant isomerization of the resulting allyl radical species. Thus, in net result, dipropylamine serves as a traceless linker agent for the deoxygenative radical cross-coupling of alkyl aldehydes with alkynes under photoredox catalysis reaction conditions. In the experiment, the researchers used many compounds, for example, 3-Iodobenzo[b]thiophene (cas: 36748-88-6Electric Literature of C8H5IS).

3-Iodobenzo[b]thiophene (cas: 36748-88-6) 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.Electric Literature of C8H5IS

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