325141-75-1

Usage

Uses

Used in Pharmaceutical Industry:
2-Acetylphenylboronic acid pinacol ester is used as a synthetic intermediate for the development of pharmaceutical compounds. Its ability to form new carbon-carbon bonds through the Suzuki-Miyaura cross-coupling reaction allows for the creation of complex organic molecules with potential therapeutic applications.
Used in Material Science Research:
2-Acetylphenylboronic acid pinacol ester is used as a building block in the synthesis of advanced materials. Its versatility in forming carbon-carbon bonds enables the development of novel materials with unique properties for various applications, such as electronics, coatings, and polymers.

Upstream product

• 98-86-2 acetophenone 
• 73183-34-3 bis(pinacol)diborane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 2142-69-0 2-bromophenyl methyl ketone 
• 577-56-0 2-acetyl-benzoic acid 
• 2142-68-9 1-(2-chlorophenyl)ethanone 
• 14428-98-9 (E)-1-phenyl-N-(1-phenylethylidene)methanamine 

Relevant academic research and scientific papers

Remarkably Efficient Iridium Catalysts for Directed C(sp2)-H and C(sp3)-H Borylation of Diverse Classes of Substrates

Here we describe the discovery of a new class of C-H borylation catalysts and their use for regioselective C-H borylation of aromatic, heteroaromatic, and aliphatic systems. The new catalysts have Ir-C(thienyl) or Ir-C(furyl) anionic ligands instead of the diamine-type neutral chelating ligands used in the standard C-H borylation conditions. It is reported that the employment of these newly discovered catalysts show excellent reactivity and ortho-selectivity for diverse classes of aromatic substrates with high isolated yields. Moreover, the catalysts proved to be efficient for a wide number of aliphatic substrates for selective C(sp3)-H bond borylations. Heterocyclic molecules are selectively borylated using the inherently elevated reactivity of the C-H bonds. A number of late-stage C-H functionalization have been described using the same catalysts. Furthermore, we show that one of the catalysts could be used even in open air for the C(sp2)-H and C(sp3)-H borylations enabling the method more general. Preliminary mechanistic studies suggest that the active catalytic intermediate is the Ir(bis)boryl complex, and the attached ligand acts as bidentate ligand. Collectively, this study underlines the discovery of new class of C-H borylation catalysts that should find wide application in the context of C-H functionalization chemistry.

Room temperature Pd(0)/Ad3P-catalyzed coupling reactions of aryl chlorides with bis(pinacolato)diboron

Room temperature Pd(0)/Ad3P-catalyzed cross-coupling reactions of aryl chlorides with bis(pinacolato)diboron are described. The Pd(0)/Ad3P catalyst, generated from Ad3P-coordinated acetanilide-based palladacycle complex, proved to be an efficient catalyst system for the Miyaura borylation reactions of a variety of aryl chlorides with bis(pinacolato)diboron. The mild reaction condition, the easy availability of the catalyst and good coupling yields make these reactions potentially useful in organic synthesis.

Ruthenium-catalyzed nitrogen-directed ortho C–H borylation of aromatic imines with pinacolborane

An efficient ruthenium catalyst system for the direct ortho C–H borylation of aromatic imines is described. The reaction of tert-butyl-1-arylmethanimines with pinacolborane in the presence of Ru(cod)(cot), followed by hydrolysis, to afford the ortho-formy

Bipolar host organic electroluminescent material and application thereof

The invention belongs to the field of organic electroluminescence, and specifically relates to a bipolar host organic electroluminescent material and an application thereof. The bipolar host organic electroluminescent material provided by the invention ha

Achieving Site Selectivity in Metal-Catalyzed Electron-Rich Carbene Transfer Reactions from N-Tosylhydrazones

Catalyst control of the site-selectivity of electron-rich alkyl, aryl disubstituted carbenes generated in situ from o-alkenyl-substituted N-tosylhydrazones was achieved in this study. Exposure of these substrates to copper iodide triggered the formation of α-alkoxy 2H-naphthalenones. This investigation established that changing the catalyst to a rhodium(II) carboxylate turned off cyclization and migration of the electron-rich metal carbene with the β-carboxylate and turned on allylic C-H bond functionalization to diastereoselectively afford 1H-indenes. Examination of the scope of this reaction revealed that ethereal, aminomethylene, and unactivated 2° C-H bonds could be functionalized.

Isonicotinate Ester Catalyzed Decarboxylative Borylation of (Hetero)Aryl and Alkenyl Carboxylic Acids through N-Hydroxyphthalimide Esters

Decarboxylative borylation of aryl and alkenyl carboxylic acids with bis(pinacolato)diboron was achieved through N-hydroxyphthalimide esters using tert-butyl isonicotinate as a catalyst under base-free conditions. A variety of aryl carboxylic acids possessing different functional groups and electronic properties can be smoothly converted to aryl boronate esters, including those that are difficult to decarboxylate under transition-metal catalysis, offering a new method enabling use of carboxylic acid as building blocks in organic synthesis. Mechanistic analysis suggests the reaction proceeds through coupling of a transient aryl radical generated by radical decarboxylation with a pyridine-stabilized persistent boryl radical. Activation of redox active esters may proceed via an intramolecular single-electron-transfer (SET) process through a pyridine-diboron-phthalimide adduct and accounts for the base-free reaction conditions.

PURINONES AS UBIQUITIN-SPECIFIC PROTEASE 1 INHIBITORS

The application relates to inhibitors of USP1 useful in the treatment of cancers, and other USP1 associated diseases and disorders, having the Formula: (I), where R1, R2, R3, R3', R4, R5, X1, X2, X3, X4, and n are described herein.

Dibenzo [c, i] [1,10] O-phenanthroline and its derivatives and preparation method

The invention discloses a dibenzo[c, i][1, 10]o-phenanthroline, its derivative and preparation method. The compound is characterized in that: two phenanthridines share a benzene ring, and the ortho-position of the nitrogen atom is equipped with a substituent group, which can be hydrogen, alkyl, phenyl or aryl. The preparation method includes: taking 4, 7-dibromobenzo[2, 1, 3]thiadiazole and 2-formyl phenylboronic acid or 2-acetyl(or arylformyl)phenylboronic acid pinacol ester as raw materials, carrying out Suzuki coupling reaction to obtain a series of 4, 7-di[2-formyl, 2-alkylformyl or arylformyl]benzo[2, 1, 3]thiadiazole, and finally carrying out reduction by sodium borohydride/cobalt chloride hexahydrate or lithium aluminum hydride and cyclization so as to obtain a series of dibenzo[c, i][1, 10]o-phenanthroline and its derivatives. The series of organic compounds provided by the invention broadens the scope of organic electroluminescent materials, and the preparation method provides a simple and convenient way for synthesis of phenanthroline series compounds. (formula).

Copper-Catalyzed Formation of α-Alkoxycycloalkenones from N-Tosylhydrazones

The combination of 20 mol % of copper iodide and lithium tert-butoxide triggers the formation of a broad range of substituted, functionalized α-alkoxy 2H-naphthalenones from readily available N-tosylhydrazones. The data suggests that this transformation occurs through cycloaddition of a copper carbenoid with an ester, followed by a Lewis acid-catalyzed [1,2] alkyl shift of the in situ generated alkoxyepoxide intermediate. The combination of 20 mol % of copper iodide and lithium tert-butoxide triggers the formation of a broad range of substituted, functionalized α-alkoxy 2H-naphthalenones from readily available N-tosylhydrazones. The reaction proceeds by the cycloaddition of a copper carbenoid with an ester, and a subsequent Lewis acid-catalyzed [1,2] alkyl shift of the in situ generated alkoxyepoxide intermediate.