325142-91-4

Usage

Uses

Used in Organic Synthesis:
2-(4-Isopropylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a crucial reagent in organic synthesis, particularly for the formation of new carbon-carbon bonds. Its ability to facilitate such bond formations makes it a valuable component in the creation of complex organic molecules.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 2-(4-Isopropylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is utilized as a key intermediate in the development of new drugs. Its role in cross-coupling reactions allows for the synthesis of diverse molecular structures with potential therapeutic applications.
Used in Agrochemical Research:
Similarly, in agrochemical research, 2-(4-Isopropylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is employed to synthesize new molecules with pesticidal or herbicidal properties. The versatility of 2-(4-Isopropylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane in creating carbon-carbon bonds is instrumental in designing novel agrochemicals to address pest and weed control challenges.
Used in Suzuki-Miyaura Cross-Coupling Reactions:
A significant application of 2-(4-Isopropylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is in the realm of Suzuki-Miyaura cross-coupling reactions, which are pivotal for the formation of carbon-carbon bonds between an organoboron compound and an organohalide or triflate. This reaction is widely used in the synthesis of biologically active molecules and materials with specific electronic or structural properties.

Upstream product

• 98-82-8 Isopropylbenzene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 73183-34-3 bis(pinacol)diborane 
• 586-61-8 4-iso-propylbromobenzene 
• 99-88-7 4-Isopropylaniline 
• 403-48-5 4-(isopropyl)benzenediazonium tetrafluoroborate 
• 86364-01-4 4-isopropylphenyl trifluoromethanesulfonate 
• 75-30-9 2-iodo-propane 
• 73852-88-7 2-(4-iodophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 76782-91-7 (4-isopropylphenyl)dibromoborane 
• 18027-97-9 Trimethyl-(2-isopropylphenyl)silane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 476156-89-5 4-(diethoxyboryl)cumene 
• 4139-78-0 4-isopropyl-N,N-dimethylaniline 

Relevant academic research and scientific papers

Mono-Phosphine Metal-Organic Framework-Supported Cobalt Catalyst for Efficient Borylation Reactions

We report a metal-organic framework (MOF) supported monoligated phosphine-cobalt complex, which is an active heterogeneous catalyst for aromatic C?H borylation and alkene hydroboration. The mono(phosphine)-Co catalyst (MOF?P?Co) was prepared by metalation of a porous triarylphosphine-functionalized MOF (MOF?P) with CoCl2 followed by activation with NaEt3BH. The MOF catalyst has a broad substrate scope with excellent functional group tolerance to afford arene- and alkyl-boronate esters in excellent yields and selectivity. MOF?P?Co gave a turnover number (TON) of 30,000 and could be recycled and reused at least 13 times in arene C?H borylation. Importantly, the attempt to prepare the homogeneous control (Ph3P?Co) using triphenylphosphine was unsuccessful due to the facile disproportionation reactions or intermolecular ligand exchanges in the solution. In contrast, the site isolation of the active mono(phosphine)-Co species within the MOF affords the robust and coordinatively unsaturated metal complexes, allowing to explore their catalytic properties and the reaction mechanism.

Remote steric control for undirected meta-selective C-H activation of arenes

Regioselective functionalization of arenes remains a challenging problem in organic synthesis. Steric interactions are often used to block sites adjacent to a given substituent, but they do not distinguish the remaining remote sites. We report a strategy

Unreactive C-N Bond Activation of Anilines via Photoinduced Aerobic Borylation

Unreactive C-N bond activation of anilines was achieved by photoinduced aerobic borylation. A diverse range of tertiary and secondary anilines were converted to aryl boronate esters in moderate to good yields with wide functional group tolerance under simple and ambient photochemical conditions. This transformation achieved the direct and facile C-N bond activation of unreactive anilines, providing a convenient and practical route transforming widely available anilines into useful aryl boronate esters.

Green phosphorescent compounds and organic electroluminescent device using same

The invention discloses green phosphorescent compounds and an organic electroluminescent device using the same. The organic electroluminescent device comprises an anode, a hole injection layer, a holetransport layer, a light emitting layer, an electron transport layer, an electron injection layer and a cathode which are sequentially deposited. The green phosphorescent compounds represented by a formula (I) as shown in the specification is used as a dopant of the light-emitting layer. In the formula (I), each of R1, R2 and R3 is one independently selected from the group consisting of hydrogen,deuterium, halogen, substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C1-C30 alkoxy groups, substituted or unsubstituted C6-C60 aryl groups and substituted or unsubstituted C3-C60 heteroaryl groups; X is selected from the group consisting of O, S, Se and SiR4R5; each of R4 and R5 is one independently selected from the group consisting of substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C1-C30 alkoxy groups, substituted or unsubstituted C6-C60 aryl groups and substituted or unsubstituted C3-C60 heteroaryl groups; X1-X8 are selected from C and N; Y is selected from substituted or unsubstituted naphthyridine; Z is selected from the group consisting of substituted or unsubstituted benzene, pyridine, pyrimidine, pyrazine and pyridazine; and n is selected from the group consisting of 0, 1 or 2.

Para-selective borylation of monosubstituted benzenes using a transient mediator

Herein, we conceptualized a transient mediator approach that has the capability of para-selective C-H functionalization of monosubstituted aromatics. This approach is enabled by in situ generation of a versatile sulfonium salt via highly electrophilic phenoxathiine or thianthrene dication intermediate which can be readily generated from its sulfoxide with trifluoromethanesulfonic anhydride. Preliminary mechanistic study implied that the remarkable para selectivity might be related to the incredible electrophilicity of thianthrene dication intermediate. The versatility of this approach was demonstrated via para-borylation of various monosubstituted simple aromatics combining the sulfonium salt formation with further photocatalyzed transformation.

Borylation of Diazonium Salts by Highly Emissive and Crystalline Carbon Dots in Water

Efficient borylation reaction of diazonium salts in water is realized for the first time by using easily prepared, highly emissive and crystalline carbon dots. Electron-donating and electron-withdrawing groups on diazonium salts were well tolerated with moderate to good conversion efficiency. Compared with widely used metal complexes, organic dyes and quantum dots, the approach presented herein uses carbon dots, which are nontoxic and possess good biological and medicinal compatibility and high reactivity. Therefore, this approach presents a new prospective use for carbon dots in green chemistry.

Photocatalyzed borylation using water-soluble quantum dots

The synthesis of arylboronates by Sandmeyer-type reactions in the presence of water still remains a significant challenge. Herein, we report the use of water-soluble MPA-capped quantum dot (QD) photocatalysts for the borylation of diazonium salts in the presence of water. A biphasic system under mild acidic conditions remains critical to prevent decomposition and competitive disulphide bond formation. The present protocol offers a broader scope of substrates and borylating agents. Additionally, this catalytic system offers a significantly high turnover number (TON). The present methodology can effectively distinguish subtle reactivity differences between boronic acids and boronates. Mechanistic investigation suggests an excited-state electron transfer pathway.

Nickel-Catalyzed C(sp2)-H Borylation of Arenes

In this study, C(sp2)-H borylation of arenes was accomplished by a nickel catalyst, resulting in good yield. Alkyl and alkoxy arenes were successfully functionalized, affording C(sp2)-H borylated compounds. It was unraveled that the well-defined abnormal N-heterocyclic carbene based Ni(II) complex breaks into Ni nanoparticles (Ni-NPs), which act as catalytically active species. A series of controlled reactions under stoichiometric conditions along with spectroscopic studies and single-crystal X-ray crystallographic study helped us to understand the formation of Ni-NPs along with formation of a boron(III) compound during this reaction.

Simple and Efficient Generation of Aryl Radicals from Aryl Triflates: Synthesis of Aryl Boronates and Aryl Iodides at Room Temperature

Despite the wide use of aryl radicals in organic synthesis, current methods to prepare them from aryl halides, carboxylic acids, boronic acids, and diazonium salts suffer from limitations. Aryl triflates, easily obtained from phenols, are promising aryl radical progenitors but remain elusive in this regard. Inspired by the single electron transfer process for aryl halides to access aryl radicals, we developed a simple and efficient protocol to convert aryl triflates to aryl radicals. Our success lies in exploiting sodium iodide as the soft electron donor assisted by light. This strategy enables the scalable synthesis of two types of important organic molecules, i.e., aryl boronates and aryl iodides, in good to high yields, with broad functional group compatibility in a transition-metal-free manner at room temperature. This protocol is anticipated to find potential applications in other aryl-radical-involved reactions by using aryl triflates as aryl radical precursors.

Iron-catalyzed C-H borylation of arenes

Well-defined iron bis(diphosphine) complexes are active catalysts for the dehydrogenative C-H borylation of aromatic and heteroaromatic derivatives with pinacolborane. The corresponding borylated compounds were isolated in moderate to good yields (25-73%) with a 5 mol% catalyst loading under UV irradiation (350 nm) at room temperature. Stoichiometric reactivity studies and isolation of an original trans-hydrido(boryl)iron complex, Fe(H)(Bpin)(dmpe)2, allowed us to propose a mechanism showing the role of some key catalytic species.