Tag: 200-300

Palladium-catalyzed Si-C bond-forming silylation of aryl iodides with hydrosilanes: an enhanced enantioselective synthesis of silicon-stereogenic silanes by desymmetrization was written by Chen, Li;Huang, Jiang-Bo;Xu, Zheng;Zheng, Zhan-Jiang;Yang, Ke-Fang;Cui, Yu-Ming;Cao, Jian;Xu, Li-Wen. And the article was included in RSC Advances in 2016.Related Products of 5460-32-2 This article mentions the following:

An enantioselective Pd-catalyzed Si-C bond-forming silylation reaction of aryl iodides with hydrosilanes for the synthesis of Si-stereogenic silanes was developed, in which a systematic optimization of a TADDOL-derived monodentate phosphoramidite ligand set resulted in the identification of a new TADDOL-derived phosphoramidite ligand that accesses chiral silanes with moderate to good yield and enantioselectivity under mild conditions. In the experiment, the researchers used many compounds, for example, 4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2Related Products of 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. 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 5460-32-2

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

Total synthesis of (±)-lythrancepine II and (±)-lythrancepine III was written by Hart, David J.;Hong, Won Pyo;Hsu, Leh Yeh. And the article was included in Journal of Organic Chemistry in 1987.Recommanded Product: 2314-37-6 This article mentions the following:

Total syntheses of the Lythraceae alkaloids (±)-lythrancepine II (I, R = H) and (±)-lythrancepine III (I, R = Ac) are described. The syntheses feature a stereoselective N-acyliminium ion cyclization of II, a mechanistically interesting Eschenmoser sulfide contraction of III (X = S) to III (X = CHCO₂Et) and construction of a 13-membered ring by using the Semmelhack-Ullmann procedure. In the experiment, the researchers used many compounds, for example, 3-Iodo-4-methoxybenzaldehyde (cas: 2314-37-6Recommanded Product: 2314-37-6).

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. 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: 2314-37-6

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

Pd-Catalyzed β-C(sp³)-H Arylation of Propionic Acid and Related Aliphatic Acids was written by Ghosh, Kiron K.;van Gemmeren, Manuel. And the article was included in Chemistry – A European Journal in 2017.Category: iodides-buliding-blocks This article mentions the following:

A generally applicable Pd-catalyzed protocol for the β-C(sp³)-H arylation of propionic acid and related α-branched aliphatic acids is reported. Enabled by the use of N-acetyl-β-alanine as ligand our protocol delivers a broad range of arylation products. Notably, the highly challenging substrate, propionic acid, which lacks any acceleration through the Thorpe-Ingold effect, can be employed as substrate with synthetically useful yields. Furthermore, the scalability and synthetic applicability of the protocol are demonstrated. In the experiment, the researchers used many compounds, for example, 4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2Category: iodides-buliding-blocks).

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. 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.Category: iodides-buliding-blocks

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

Small organic molecules with tailored structures: initiators in the transition-metal-free C-H arylation of unactivated arenes was written by Liu, Zhenghui;Wang, Peng;Chen, Yu;Yan, Zhenzhong;Chen, Suqing;Chen, Wenjun;Mu, Tiancheng. And the article was included in RSC Advances in 2020.Recommanded Product: 22918-03-2 This article mentions the following:

In this article, an optimized catalytically active mol., (2-(methylamino)phenyl)methanol, was designed. A broad range of aryl iodides RI (R = 2-fluorophenyl, thiophen-3-yl, pyridin-4-yl, etc.) could be converted into the corresponding arylated products RR¹ (R¹ = Ph, 4-methylphenyl) at 100°C over 24 h with good to excellent yields. Mechanistic experiments verified that radicals participated in this catalytic transformation and that the cleavage of the aromatic C-H bond was not the rate determining step. A K⁺ capture experiment by 18-crown-6 emphasized the significance of the cation species of the strong base. Fourier transform IR spectroscopy proved that the catalytic system was activated by the hydrogen bonds between small organic mols. and ^tBuOK. Also, a clear mechanism was proposed. This transition-metal-free method affords a promising system for efficient and inexpensive synthesis of biaryls via a user-friendly approach, as confirmed by scale-up experiments In the experiment, the researchers used many compounds, for example, 4-Chloro-2-iodopyridine (cas: 22918-03-2Recommanded Product: 22918-03-2).

4-Chloro-2-iodopyridine (cas: 22918-03-2) 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. 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: 22918-03-2

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

Copper(I)-Catalyzed Asymmetric Alkylation of Unsymmetrical Secondary Phosphines was written by Zhang, Shuai;Xiao, Jun-Zhao;Li, Yan-Bo;Shi, Chang-Yun;Yin, Liang. And the article was included in Journal of the American Chemical Society in 2021.Formula: C4H8ClI This article mentions the following:

A Cu(I)-catalyzed asym. alkylation of HPAr¹Ar² with alkyl halides is uncovered, which provides an array of P-stereogenic phosphines in generally high yield and enantioselectivity. The electrophilic alkyl halides enjoy a broad substrate scope, including allyl bromides, propargyl bromide, benzyl bromides, and alkyl iodides. Also, 11 unsym. diarylphosphines (HPAr¹Ar²) serve as competent pronucleophiles. The present methodol. is also successfully applied to catalytic asym. double and triple alkylation, and the corresponding products were obtained in moderate diastereo- and excellent enantioselectivities. Some ³¹P NMR experiments indicate that bulky HPPhMes exhibits weak competitively coordinating ability to the Cu(I)-bisphosphine complex, and thus the presence of stoichiometric HPAr¹Ar² does not affect the enantioselectivity significantly. Therefore, the high enantioselectivity in this reaction is attributed to the high performance of the unique Cu(I)-(R,R_P)-TANIAPHOS complex in asym. induction. Finally, one monophosphine and two bisphosphines prepared by the present reaction are employed as efficient chiral ligands to afford three structurally diversified Cu(I) complexes, which demonstrates the synthetic utility of the present methodol. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9Formula: C4H8ClI).

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. 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.Formula: C4H8ClI

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

Total syntheses of the meta,meta-bridged biphenyls (±)-myricanol and myricanone, and of an isomeric biphenyl ether, a 14-oxa[7,1]metaparacyclophane was written by Whiting, Donald A.;Wood, Andrew F.. And the article was included in Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) in 1980.Computed Properties of C8H7IO2 This article mentions the following:

Intramol. reductive coupling with (Ph₃P)₄Ni of the bisiodides I (R = R³ = iodo, R¹ = H, R² = OAc; R = R³ = iodo, R¹R² = O), derived from the phenols I (R = R¹ = R³ = H, R² = OH; R = R³ = H, R¹R² = O) gave the meta,meta-bridged biphenyls myricanone (II; R = R¹ = H, R² = OH) and (±)-myricanol (II; R = R¹ = H, R² = OH), resp., in low yields. The bridged biphenyls II (R = Me, R¹R² = O; R = Me, R¹ = H, R² = OH) were similarly prepared Irradiation at 254 nm of the bromides I (R = Br, R¹ = R³ = H, R² = OAc; R = Br, R¹R² = O, R³ = H) also induced aryl-aryl coupling to form the bridged biphenyls II (R = PhCH₂, R¹ = H, R² = OH; R = PhCH₂, R¹R² = O), resp. 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. 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.Computed Properties of C8H7IO2

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

Electrochemical Fluorination of Vinyl Boronates through Donor-Stabilized Vinyl Carbocation Intermediates was written by Wigman, Benjamin;Lee, Woojin;Wei, Wenjing;Houk, Kendall N.;Nelson, Hosea M.. And the article was included in Angewandte Chemie, International Edition in 2022.Recommanded Product: 5460-32-2 This article mentions the following:

The electrochem. generation of vinyl carbocations RC(F)=C(R¹)R² (R = 4-methoxyphenyl, thiophen-2-yl, 2,2-dimethyl-2H-1,3-benzodioxol-5-yl, etc.; R¹ = R² = n-Bu, 4-methoxyphenyl; R¹R² = -(CH₂)₄-, -(CH₂)₅-) from alkenyl boronic esters and boronates RC(Bpin)=C(R¹)R² is reported. Using easy-to-handle nucleophilic fluoride reagents, these intermediates are trapped to form fully substituted vinyl fluorides. Mechanistic studies support the formation of dicoordinated carbocations through sequential single-electron oxidation events. Notably, this electrochem. fluorination features fast reaction times and Lewis acid-free conditions. This transformation provides a complementary method to access vinyl fluorides with simple fluoride salts such as TBAF. 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. 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.Recommanded Product: 5460-32-2

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

Triflic acid catalysed regioselective synthesis of substituted naphthalenes by benzannulation of carbonyls with alkynes was written by Gudla, Vanajakshi;Sudheer, Mokhamatam;Rao, Chinthu Joginarayana;Sanasi, Paul Douglas;Battula, Venkateswara Rao. And the article was included in Tetrahedron in 2021.Name: 4-Iodo-1,2-dimethoxybenzene This article mentions the following:

An interesting and facile triflic acid catalyzed annulation of α-aryl carbonyls with arylalkynes was presented for the regioselective synthesis of substituted naphthalenes. The annulation reaction involved a sequence of electrophilic attack of carbonyl on arylalkyne and benzannulation catalyzed by triflic acid. The present catalyst effects this transformation at room temperature itself. Intramol. version of the present Bronsted acid catalysis furnished compounds containing 1-arylnaphthalene core fused with ring systems in excellent yields. 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. 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.Name: 4-Iodo-1,2-dimethoxybenzene

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

Total Synthesis of Isohericenone J via a Stille Coupling Reaction was written by Cao, Wei;Chen, Ping;Tang, Yu. And the article was included in Journal of Natural Products in 2020.Recommanded Product: Methyl 3,5-dihydroxy-4-iodobenzoate This article mentions the following:

The first total synthesis of isohericenone J is reported. Key features of this synthetic strategy are a Friedel-Crafts reaction to construct the isobenzofuranone unit and a Pd-catalyzed Stille coupling reaction for the formation of the C5-C1′ bond, generating the natural product, as well as one of its isomers, in 6.0% overall yield in eight steps. This strategy provides a foundation for the synthesis of challenging isobenzofuranone and isoindolinone-type derivatives In the experiment, the researchers used many compounds, for example, Methyl 3,5-dihydroxy-4-iodobenzoate (cas: 338454-02-7Recommanded Product: Methyl 3,5-dihydroxy-4-iodobenzoate).

Methyl 3,5-dihydroxy-4-iodobenzoate (cas: 338454-02-7) 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.Recommanded Product: Methyl 3,5-dihydroxy-4-iodobenzoate

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

A Polar Substituent-Containing Acylation Agent for the Radioiodination of Internalizing Monoclonal Antibodies: N-Succinimidyl 4-Guanidinomethyl-3-[¹³¹I]iodobenzoate ([¹³¹I]SGMIB) was written by Vaidyanathan, Ganesan;Affleck, Donna J.;Li, Jean;Welsh, Phil;Zalutsky, Michael R.. And the article was included in Bioconjugate Chemistry in 2001.Application In Synthesis of 5-Iodonicotinic acid This article mentions the following:

The objective of this study was to develop an acylation agent for the radioiodination of monoclonal antibodies that would maximize retention of the label in tumor cells following receptor- or antigen-mediated internalization. The strategy taken was to add a polar substituent to the labeled aromatic ring to impede transport of labeled catabolites across lysosomal and cell membranes after antibody degradation Preparation of unlabeled N-succinimidyl 4-guanidinomethyl-3-iodobenzoate (SGMIB) was achieved in six steps from 3-iodo-4-methylbenzoic acid. Preparation of 4-guanidinomethyl-3-[¹³¹I]iodobenzoic acid from the silicon precursor, 4-(N¹,N²-bis-tert-butyloxycarbonyl)guanidinomethyl-3-trimethylsilylbenzoic acid proceeded in less than 5% radiochem. yield. A more successful approach was to prepare [¹³¹I]SGMIB directly from the tin precursor, N-succinimidyl 4-(N¹,N²-bis-tert-butyloxycarbonyl)guanidinomethyl-3-trimethylstannylbenzoate, which was achieved in 60-65% radiochem. yield. A rapidly internalizing anti-epidermal growth factor receptor variant III antibody L8A4 was labeled using [¹³¹I]SGMIB in 65% conjugation efficiency and with preservation of immunoreactivity. Paired-label in vitro internalization assays demonstrated that the amount of radioactivity retained in cells after internalization for L8A4 labeled with [¹³¹I]SGMIB was 3-4-fold higher than that for L8A4 labeled with ¹²⁵I using either Iodogen or [¹²⁵I]SIPC. Catabolite assays documented that the increased retention of radioiodine in tumor cells for antibody labeled using [¹³¹I]SGMIB was due to pos. charged, low mol. weight species. These results suggest that [¹³¹I]SGMIB warrants further evaluation as a reagent for labeling internalizing antibodies. In the experiment, the researchers used many compounds, for example, 5-Iodonicotinic acid (cas: 15366-65-1Application In Synthesis of 5-Iodonicotinic acid).

5-Iodonicotinic acid (cas: 15366-65-1) belongs to iodide derivatives. Iodide-containing intermediates are common in organic synthesis, because of the easy formation and cleavage of the C–I bond. 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.Application In Synthesis of 5-Iodonicotinic acid

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