Category: 1214264-88-6

Copper-Photocatalyzed Hydroboration of Alkynes and Alkenes was written by Zhong, Mingbing;Gagne, Yohann;Hope, Taylor O.;Pannecoucke, Xavier;Frenette, Mathieu;Jubault, Philippe;Poisson, Thomas. And the article was included in Angewandte Chemie, International Edition in 2021.COA of Formula: C16H20B2N2O2 This article mentions the following:

The photocatalytic hydroboration of alkenes and alkynes is reported. The use of newly-designed copper photocatalysts with B₂Pin₂ permits the formation a boryl radical, which is used for hydroboration of a large panel of alkenes and alkynes. The hydroborated products were isolated in high yields, with excellent diastereoselectivities and a high functional group tolerance under mild conditions. The hydroboration reactions were developed under continuous flow conditions to demonstrate their synthetic utility. The reaction mechanism was studied and suggested an oxidation reaction between an in situ formed borate and the Cu-photocatalyst in its excited state for the boryl radical formation. In the experiment, the researchers used many compounds, for example, 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine (cas: 1214264-88-6COA of Formula: C16H20B2N2O2).

2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine (cas: 1214264-88-6) belongs to alcohols. Alkyl halides are often synthesized from alcohols, in effect substituting a halogen atom for the hydroxyl group. Secondary alcohols are easily oxidized without breaking carbon-carbon bonds only as far as the ketone stage. No further oxidation is seen except under very stringent conditions.COA of Formula: C16H20B2N2O2

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Copper-Catalyzed Protoboration of 1,3-Diynes as a Platform for Iterative Functionalization was written by Ghosh, Suman;Chakrabortty, Rajesh;Kumar, Shailendra;Das, Aniruddha;Ganesh, Venkataraman. And the article was included in ACS Catalysis in 2022.Electric Literature of C16H20B2N2O2 This article mentions the following:

This paper presents the protoboration of 1,3-diynes as a platform for the iterative functionalization of various groups on enynes and dienes. Synthetic approaches to targets with high complexity are directed toward using small, modular building blocks similar to a Lego construction using iterative chem. and automated synthesis. Organoboron compounds are currently in the spotlight for achieving these goals. Here, the authors report an operationally simple, regioselective protoboration of 1,3-diynes using a mixed diboron reagent and Cu(I)/phosphine catalyst to provide enynylboronates in good yields. Under similar conditions, diprotoboration of 1,3-diynes was also achieved to access bench-stable 1,4-diboryl-1,3-dienes in good yields and regioselectivities. The iterative coupling capabilities of the products were demonstrated along with other downstream transformations offering a range of value-added skeletons. In the experiment, the researchers used many compounds, for example, 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine (cas: 1214264-88-6Electric Literature of C16H20B2N2O2).

2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine (cas: 1214264-88-6) belongs to alcohols. Alcohols are weak acids. The most acidic simple alcohols (methanol and ethanol) are about as acidic as water, and most other alcohols are somewhat less acidic. Converting an alcohol to an alkene requires removal of the hydroxyl group and a hydrogen atom on the neighbouring carbon atom. Dehydrations are most commonly carried out by warming the alcohol in the presence of a strong dehydrating acid, such as concentrated sulfuric acid.Electric Literature of C16H20B2N2O2

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Copper-catalyzed B(dan)-installing carboboration of alkenes was written by Kageyuki, Ikuo;Osaka, Itaru;Takaki, Ken;Yoshida, Hiroto. And the article was included in Organic Letters in 2017.HPLC of Formula: 1214264-88-6 This article mentions the following:

Carboboration of alkenes was found to occur readily with an unsym. diboron [(pin)B-B(dan)] (H₂dan = 1,8-naphthalenediamine) and alkyl halides under copper catalysis, leading to the direct formation of protected alkylboron compounds via synchronous C-C and C-B bond-forming processes. The B(dan) moiety was solely installed into the organic frameworks with the regioselective attachment to a terminal carbon of alkenes employed. In the experiment, the researchers used many compounds, for example, 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine (cas: 1214264-88-6HPLC of Formula: 1214264-88-6).

2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine (cas: 1214264-88-6) belongs to alcohols. The oxygen atom of the strongly polarized O―H bond of an alcohol pulls electron density away from the hydrogen atom. This polarized hydrogen, which bears a partial positive charge, can form a hydrogen bond with a pair of nonbonding electrons on another oxygen atom. A multistep synthesis may use Grignard-like reactions to form an alcohol with the desired carbon structure, followed by reactions to convert the hydroxyl group of the alcohol to the desired functionality.HPLC of Formula: 1214264-88-6

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Trans-Diborylation of Alkynes: Pseudo-Intramolecular Strategy Utilizing a Propargylic Alcohol Unit was written by Nagashima, Yuki;Hirano, Keiichi;Takita, Ryo;Uchiyama, Masanobu. And the article was included in Journal of the American Chemical Society in 2014.Quality Control of 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine This article mentions the following:

Authors present the first trans-selective diborylation reaction of alkynes. By theor. calculation-assisted reaction anal., authors designed a pseudo-intramol. reaction of diboron, propargyl alc., and a base to facilitate B-B bond activation and C-B bond formation with high efficiency. This approach provides synthetically versatile and densely functionalized 4-borylated 1,2-oxaborol-2(5H)-oles (vinyldiboronates) in a straightforward manner. Detailed computational anal. showed that the directing alkoxide functionality markedly lowers the activation energy of B-C bond formation. In the experiment, the researchers used many compounds, for example, 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine (cas: 1214264-88-6Quality Control of 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine).

2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine (cas: 1214264-88-6) belongs to alcohols. The oxygen atom of the strongly polarized O―H bond of an alcohol pulls electron density away from the hydrogen atom. This polarized hydrogen, which bears a partial positive charge, can form a hydrogen bond with a pair of nonbonding electrons on another oxygen atom. Under carefully controlled conditions, simple alcohols can undergo intermolecular dehydration to give ethers. This reaction is effective only with methanol, ethanol, and other simple primary alcohols.Quality Control of 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Copper-Catalyzed Asymmetric Borylative Ring Opening of Diazabicycles was written by Lee, Hyesu;Han, Jung Tae;Yun, Jaesook. And the article was included in ACS Catalysis in 2016.COA of Formula: C16H20B2N2O2 This article mentions the following:

Highly enantioselective, copper-catalyzed ring opening of bicyclic hydrazines using a diboron reagent was accomplished with (R,R)-taniaphos as a chiral ligand. Desymmetrization of various bicyclic hydrazines by boryl substitution afforded 3-Bpin-4-hydrazino-cyclopentene derivatives with enantioselectivity up to >99% under mild conditions. The resulting allylic boron products were utilized in further organic transformations. Kinetic resolution of a racemic bicyclic oxazine gave useful information about the relative rates of C-O and C-N bond cleavage. In the experiment, the researchers used many compounds, for example, 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine (cas: 1214264-88-6COA of Formula: C16H20B2N2O2).

2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine (cas: 1214264-88-6) belongs to alcohols. Under appropriate conditions, inorganic acids also react with alcohols to form esters. To form these esters, a wide variety of specialized reagents and conditions can be used. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.COA of Formula: C16H20B2N2O2

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Substrate-Assisted, Transition-Metal-Free Diboration of Alkynamides with Mixed Diboron: Regio- and Stereoselective Access to trans-1,2-Vinyldiboronates was written by Verma, Astha;Snead, Russell F.;Dai, Yumin;Slebodnick, Carla;Yang, Yinuo;Yu, Haizhu;Yao, Fu;Santos, Webster L.. And the article was included in Angewandte Chemie, International Edition in 2017.Application In Synthesis of 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine This article mentions the following:

A substrate-assisted diboration of alkynamides using the unsym. pinacolato-1,8-diaminonaphthalenato diboron (pinBBdan) is described. The transition-metal-free reaction proceeds in a regio- and stereoselective fashion to exclusively afford trans-vinyldiboronates in good to excellent yields. Notably, Bdan and Bpin are installed on the α- and β-carbon atoms, resp. In the experiment, the researchers used many compounds, for example, 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine (cas: 1214264-88-6Application In Synthesis of 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine).

2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine (cas: 1214264-88-6) belongs to alcohols. Similar to water, an alcohol can be pictured as having an sp3 hybridized tetrahedral oxygen atom with nonbonding pairs of electrons occupying two of the four sp3 hybrid orbitals. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.Application In Synthesis of 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Silaboration of [1.1.1]Propellane: A Storable Feedstock for Bicyclo[1.1.1]pentane Derivatives was written by Kondo, Masaki;Kanazawa, Junichiro;Ichikawa, Tomohiro;Shimokawa, Takumi;Nagashima, Yuki;Miyamoto, Kazunori;Uchiyama, Masanobu. And the article was included in Angewandte Chemie, International Edition in 2020.Electric Literature of C16H20B2N2O2 This article mentions the following:

The silaboration of [1.1.1]propellane enables direct introduction of B and Si functional groups onto the bicyclo[1.1.1]pentane (BCP) scaffold in high yield under mild, additive-free conditions. The silaborated BCP can be obtained on a gram-scale in a single step without the need for column-chromatog. purification, and is storable and easy to handle, providing a versatile synthetic intermediate for BCP derivatives We also describe various conversions of the C-B/C-Si bonds on the BCP scaffold, including development of a modified Suzuki-Miyaura cross-coupling reaction at the highly sterically hindered bridgehead sp³ carbon center of the BCP skeleton using a combination of highly activated BCP boronic esters, copper(I) oxide, and a PdCl₂(dppf) catalyst system. In the experiment, the researchers used many compounds, for example, 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine (cas: 1214264-88-6Electric Literature of C16H20B2N2O2).

2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine (cas: 1214264-88-6) belongs to alcohols. The oxygen atom of the strongly polarized O―H bond of an alcohol pulls electron density away from the hydrogen atom. This polarized hydrogen, which bears a partial positive charge, can form a hydrogen bond with a pair of nonbonding electrons on another oxygen atom. The most common reactions of alcohols can be classified as oxidation, dehydration, substitution, esterification, and reactions of alkoxides.Electric Literature of C16H20B2N2O2

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts