Category: 214360-63-1

COA of Formula: C14H21BO3On June 12, 2017, Zhu, Lei; Qi, Xiaotian; Li, Yingzi; Duan, Meng; Zou, Lufeng; Bai, Ruopeng; Lan, Yu published an article in Organometallics. The article was 《Ir(III)/Ir(V) or Ir(I)/Ir(III) Catalytic Cycle? Steric-Effect-Controlled Mechanism for the para-C-H Borylation of Arenes》. The article mentions the following:

A potential energy surface for iridium-catalyzed C-H-borylation of aromatic compounds was calculated; while bulky phosphine ligands favor Ir(I)-Ir(III) C-H activation, small amine ligands promote formation of triboryl Ir(V) intermediates. D. functional theory method N12 was used to study the mechanism of the [Ir(cod)OH]2/Xyl-MeO-BIPHEP-catalyzed para-selective C-H borylation reaction. The results revealed that the use of a bulky diphosphine ligand such as Xyl-MeO-BIPHEP was unfavorable for the previously proposed iridium(III)/iridium(V) catalytic cycle because it resulted in considerable steric repulsion in the hepta-coordinated iridium(V) intermediate. Inspired by this steric effect, we have proposed a novel iridium(I)/iridium(III)-based catalytic cycle for this transformation and shown that it can be used to account for the exptl. results. The iridium(I)/iridium(III) catalytic cycle induced by this steric effect consists of several steps, including: (i) the oxidative addition of the C-H bond of the substrate to an active iridium(I) boryl complex; (ii) the reductive elimination of a C-B bond; (iii) the oxidative addition of B2pin2 to an iridium(I) hydride complex; and (iv) the reductive elimination of a B-H bond. Notably, the computed regioselectivity of this reaction was consistent with the exptl. observations. The high para-selectivity of this reaction was also explained using structural anal. and a 2D contour model, which revealed that the strong steric repulsion between the diphosphine ligand and the meta-substituents resulted in a higher energy barrier for meta-C-H activation. The experimental process involved the reaction of 2-(4-Methoxy-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(cas: 214360-63-1COA of Formula: C14H21BO3)

2-(4-Methoxy-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(cas: 214360-63-1) belongs to ethers.Oxygen is more electronegative than carbon, thus the alpha hydrogens of ethers are more acidic than those of simple hydrocarbons. They are far less acidic than alpha hydrogens of carbonyl groups (such as in ketones or aldehydes), however. COA of Formula: C14H21BO3

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

《Iridium-catalyzed C-H borylation of quinolines and unsymmetrical 1,2-disubstituted benzenes: insights into steric and electronic effects on selectivity》 was published in Chemical Science in 2012. These research results belong to Tajuddin, Hazmi; Harrisson, Peter; Bitterlich, Bianca; Collings, Jonathan C.; Sim, Neil; Batsanov, Andrei S.; Cheung, Man Sing; Kawamorita, Soichiro; Maxwell, Aoife C.; Shukla, Lena; Morris, James; Lin, Zhenyang; Marder, Todd B.; Steel, Patrick G.. Computed Properties of C14H21BO3 The article mentions the following:

Borylation of quinolines provides an attractive method for the late-stage functionalization of this important heterocycle. The regiochem. of this reaction is dominated by sterptsic factors but, by undertaking reactions at room temperature, an underlying electronic selectivity becomes apparent, as exemplified by the comparative reactions of 7-halo-2-methylquinoline and 2,7-dimethylquinoline which afford variable amounts of the 5- and 4-borylated products. Similar electronic selectivities are observed for nonsym. 1,2-disubstituted benzenes. The site of borylation can be simply estimated by anal. of the 1H NMR spectrum of the starting material with preferential borylation occurring at the site of the most deshielded sterically accessible H or C atom. Such effects can be linked with C-H acidity. While DFT calculations of the pKa for the C-H bond show good correlation with the observed selectivity, small differences suggest that related alternative, but much more computationally demanding values, such as the M-C bond strength, may be better quant. predictors of selectivity.2-(4-Methoxy-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(cas: 214360-63-1Computed Properties of C14H21BO3) was used in this study.

2-(4-Methoxy-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(cas: 214360-63-1) belongs to ethers.Computed Properties of C14H21BO3Although ethers resist hydrolysis, they are cleaved by hydrobromic acid and hydroiodic acid. Hydrogen chloride cleaves ethers only slowly.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Che, Jinxin; Jin, Zegao; Yan, Fangjie; You, Jieqiong; Xie, Jiangfeng; Chen, Binhui; Cheng, Gang; Zhu, Hong; He, Qiaojun; Hu, Yongzhou; Yang, Bo; Cao, Ji; Dong, Xiaowu published an article in Journal of Medicinal Chemistry. The title of the article was 《Discovery of 5,6-Bis(4-methoxy-3-methylphenyl)pyridin-2-amine as a WSB1 Degrader to Inhibit Cancer Cell Metastasis》.Computed Properties of C14H21BO3 The author mentioned the following in the article:

The gain of cell motility is an essential prerequisite for cancer metastasis. The ubiquitin ligase subunit WD repeat and SOCS box-containing 1 (WSB1) has been demonstrated to regulate hypoxia-driven tumor cell migration. However, there is still a lack of methods for discovering inhibitors targeting the WSB1 axis. Here, we employed phenotypic screening models and identified compound 4 that displayed migration inhibitory activity against WSB1-overexpressing cells. Further studies indicated that it may function as a WSB1 degrader, thus leading to the accumulation of the Rho guanosine diphosphate dissociation inhibitor 2 (RhoGDI2) protein, reversing the expression of downstream F-actin and formation of membrane ruffles, and disturbing the migration capacity of cancer cells. Moreover, compound 4 exhibited a promising in vivo anticancer metastatic effects. Our findings show the discovery of a new WSB1 degrader, providing a unique solution for the treatment of cancer metastasis. In the experiment, the researchers used 2-(4-Methoxy-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(cas: 214360-63-1Computed Properties of C14H21BO3)

2-(4-Methoxy-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(cas: 214360-63-1) belongs to ethers.Computed Properties of C14H21BO3Although ethers resist hydrolysis, they are cleaved by hydrobromic acid and hydroiodic acid. Hydrogen chloride cleaves ethers only slowly.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Cheng, Chen; Hartwig, John F. published an article on February 21 ,2014. The article was titled 《Rhodium-Catalyzed Intermolecular C-H Silylation of Arenes with High Steric Regiocontrol》, and you may find the article in Science (Washington, DC, United States).Electric Literature of C14H21BO3 The information in the text is summarized as follows:

Regioselective C-H functionalization of arenes has widespread applications in synthetic chem. The regioselectivity of these reactions is often controlled by directing groups or steric hindrance ortho to a potential reaction site. Here, authors report a catalytic intermol. C-H silylation of unactivated arenes that manifests very high regioselectivity through steric effects of substituents meta to a potential site of reactivity. The silyl moiety can be further functionalized under mild conditions but is also inert toward many common organic transformations, rendering the silylarene products useful building blocks. The remote steric effect that we observe results from the steric properties of both the rhodium catalyst and the silane. In the experiment, the researchers used 2-(4-Methoxy-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(cas: 214360-63-1Electric Literature of C14H21BO3)

2-(4-Methoxy-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(cas: 214360-63-1) belongs to ethers. Ethers lack the hydroxyl groups of alcohols. Without the strongly polarized O―H bond, ether molecules cannot engage in hydrogen bonding with each other. Electric Literature of C14H21BO3

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

《para-C-H Borylation of benzene derivatives by a bulky iridium catalyst》 was written by Saito, Yutaro; Segawa, Yasutomo; Itami, Kenichiro. SDS of cas: 214360-63-1 And the article was included in Journal of the American Chemical Society on April 22 ,2015. The article conveys some information:

A highly para-selective aromatic C-H borylation has been accomplished. By a new iridium catalyst bearing a bulky diphosphine ligand, Xyl-MeO-BIPHEP, the C-H borylation of monosubstituted benzenes can be affected with para-selectivity up to 91%. This catalytic system is quite different from the usual iridium catalysts that cannot distinguish meta- and para-C-H bonds of monosubstituted benzene derivatives, resulting in the preferred formation of meta-products. The para-selectivity increases with increasing bulkiness of the substituent on the arene, indicating that the regioselectivity of the present reaction is primarily controlled by steric repulsion between substrate and catalyst. Caramiphen, an anticholinergic drug used in the treatment of Parkinson’s disease, was converted into five derivatives via our para-selective borylation. The present [Ir(cod)OH]2/Xyl-MeO-BIPHEP catalyst represents a unique, sterically controlled, para-selective, aromatic C-H borylation system that should find use in streamlined, predictable chem. synthesis and in the rapid discovery and optimization of pharmaceuticals and materials. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxy-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(cas: 214360-63-1SDS of cas: 214360-63-1)

2-(4-Methoxy-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(cas: 214360-63-1) belongs to ethers.Oxygen is more electronegative than carbon, thus the alpha hydrogens of ethers are more acidic than those of simple hydrocarbons. SDS of cas: 214360-63-1 They are far less acidic than alpha hydrogens of carbonyl groups (such as in ketones or aldehydes), however.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

《Borylation of Unactivated Aryl Chlorides under Mild Conditions by Using Diisopropylaminoborane as a Borylating Reagent》 was written by Guerrand, Helene D. S.; Marciasini, Ludovic D.; Jousseaume, Melissa; Vaultier, Michel; Pucheault, Mathieu. Synthetic Route of C14H21BO3 And the article was included in Chemistry – A European Journal in 2014. The article conveys some information:

The synthesis of arylboronic ester derivatives from aryl chlorides by using aryl(amino)boranes is described. Palladium-catalyzed coupling between aryl chlorides and diisopropylaminoborane leads to the formation of a C-B bond under mild conditions. A wide range of functional groups are tolerated, making this method particularly useful for the borylation of functionalized aromatics In the experiment, the researchers used many compounds, for example, 2-(4-Methoxy-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(cas: 214360-63-1Synthetic Route of C14H21BO3)

2-(4-Methoxy-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(cas: 214360-63-1) belongs to ethers.Ethers do have nonbonding electron pairs on their oxygen atoms, and they can form hydrogen bonds with other molecules (alcohols, amines, etc.) that have O―H or N―H bonds. The ability to form hydrogen bonds with other compounds makes ethers particularly good solvents for a wide variety of organic compounds and a surprisingly large number of inorganic compounds.Synthetic Route of C14H21BO3

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem