1381960-58-2

Usage

Uses

Used in Organic Synthesis:
4,4,5,5-TetraMethyl-2-[4-(4-Methylphenyl)phenyl]-1,3,2-dioxaborolane is used as a reagent in the Suzuki-Miyaura cross-coupling reaction for the formation of carbon-carbon bonds. Its high stability and selective reactivity make it a valuable tool in the synthesis of complex organic molecules.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 4,4,5,5-TetraMethyl-2-[4-(4-Methylphenyl)phenyl]-1,3,2-dioxaborolane is used as a key intermediate in the development of new drugs and biologically active molecules. Its unique structure and properties contribute to the discovery and synthesis of novel therapeutic agents.
Used in Materials Science:
4,4,5,5-TetraMethyl-2-[4-(4-Methylphenyl)phenyl]-1,3,2-dioxaborolane is utilized in materials science for the synthesis of advanced materials with specific properties. Its unique structure allows for the development of materials with tailored characteristics for various applications.
Used in Catalysis:
In the field of catalysis, 4,4,5,5-TetraMethyl-2-[4-(4-Methylphenyl)phenyl]-1,3,2-dioxaborolane is employed as a catalyst or catalyst precursor in various chemical reactions. Its unique properties enable the development of efficient and selective catalytic processes for the synthesis of desired products.

Upstream product

• 5720-05-8 4-methylphenylboronic acid 
• 586-77-6 4-bromo-N,N-dimethylaniline 
• 141082-00-0 4-dimethylamino-4'-methylbiphenyl 
• 73183-34-3 bis(pinacol)diborane 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 50670-49-0 4-bromo-4'-methylbiphenyl 
• 613-33-2 (4,4'-dimethyl-1,1'-biphenyl) 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 72093-43-7 4-methyl-4'-fluorobiphenyl 
• 100-01-6 4-nitro-aniline 
• 106-38-7 para-bromotoluene 
• 171364-83-3 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene 
• 214360-73-3 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline 

Downstream Products

• 207611-87-8 4,4′-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1′-biphenyl 

Relevant academic research and scientific papers

Photoinduced Deaminative Borylation of Unreactive Aromatic Amines Enhanced by CO2

Herein, direct unreactive C-N borylation of aromatic amines by a photocatalyst was achieved. The C-N borylation of aromatic amines with bis(pinacolato)diboron (B2pin2) proceeded using a pyrene catalyst under light irradiation to afford desired borylated products and aminoborane as a byproduct. The yield of the borylated product improved under a CO2 atmosphere which probably reduced the inhibitory effect of aminoborane. Mechanistic studies suggested that the C-N bond cleavage and C-B bond formation proceeded via a concerted pathway.

End-Functionalization of Diarylethene for Opto-Electronic Switching with High Fatigue Resistance

A molecular and synthetic approach to strengthen the switching performance of diarylethene (DAE)-based organic transistors is proposed. By tuning the length of alkyl side chains of the biphenyl unit attached to 1,2-bis(5-biphenyl-2-methylthien-3-yl)perfluorocyclopentene (DAE), we show that the molecular environment for reversible photoisomerization of DAEs can be optimized. Four different DAEs are synthesized with different alkyl chains (DAE_C0, DAE_C1, DAE_C6, and DAE_C10), and ITIC is chosen to construct a semiconductor matrix to maximize the quantum yield of photoconversion considering the complementary absorption range of both materials. From photophysical, structural, and morphological analyses, the longer alkyl chains inhibit intermolecular aggregation between DAEs and allow more hydrophobic surface properties of DAEs, thus improving molecular miscibility with ITIC. The improved molecular compatibility of DAEs with ITIC makes the overall bulk heterojunction film amorphous, allowing more free volume for reversible photoisomerization. Consequently, DAE_C6 exhibits the maximum quantum yield for both photocyclization and photocycloreversion, enabling high light-controlled on/off ratios in photoswitchable transistors. Furthermore, the exceptionally high DAE_C6 quantum yield enables robust fatigue resistance under repeated photoswitching with only a 30% decrease in the on/off ratio after 100 cycles. Overall, this work shows that not only the energy level but also the molecular compatibility can endow significant switching performances for molecular switches.

Cleavage of C(aryl)?CH3 Bonds in the Absence of Directing Groups under Transition Metal Free Conditions

Organic chemists now can construct carbon–carbon σ-bonds selectively and sequentially, whereas methods for the selective cleavage of carbon–carbon σ-bonds, especially for unreactive hydrocarbons, remain limited. Activation by ring strain, directing groups, or in the presence of a carbonyl or a cyano group is usually required. In this work, by using a sequential strategy site-selective cleavage and borylation of C(aryl)?CH3 bonds has been developed under directing group free and transition metal free conditions. Methyl groups of various arenes are selectively cleaved and replaced by boryl groups. Mechanistic analysis suggests that it proceeds by a sequential intermolecular oxidation and coupling of a transient aryl radical, generated by radical decarboxylation, involving a pyridine-stabilized persistent boryl radical.

Metal-Free and Redox-Neutral Conversion of Organotrifluoroborates into Radicals Enabled by Visible Light

Converting organoboron compounds into the corresponding radicals has broad synthetic applications in organic chemistry. To achieve these transformations, various strong oxidants such as Mn(OAc)3, AgNO3/K2S2O8, and Cu(OAc)2, in stoichiometric amounts are required, proceeding by a single-electron transfer mechanism. Established herein is a distinct strategy for generating both aryl and alkyl radicals from organotrifluoroborates through an SH2 process. This strategy is enabled by using water as the solvent, visible light as the energy input, and diacetyl as the promoter in the absence of any metal catalyst or redox reagent, thereby eliminating metal waste. To demonstrate its synthetic utility, an efficient acetylation to prepare valuable aryl (alkyl) methyl ketones is described and applications to construct C?C, C?I, C?Br, and C?S bonds are also feasible. Experimental evidence suggests that triplet diacetyl serves as the key intermediate in this process.

LiHMDS-Promoted Palladium or Iron-Catalyzed ipso-Defluoroborylation of Aryl Fluorides

A novel and efficient method for the synthesis of arylboronic acid pinacol esters via a palladium- or iron-catalyzed cross-coupling reaction of aryl fluorides with bis(pinacolato)diboron (B2pin2) in the presence of LiHMDS was developed. The Pd-catalyzed defluoroborylation of fluoroarenes is compatible with a variety of functional groups such as primary and secondary amine, ketone, trifluoromethyl, alkoxy, and boryl. Remarkably, no external ligand is required for enhanced conversion efficiency.

Copper-Catalyzed ipso-Borylation of Fluoroarenes

ipso-Borylation of fluoroarenes has been achieved using an air-stable copper complex as a catalyst. Mechanistic studies suggest that the reaction proceeds via an SRN1 mechanism involving a single-electron-transfer (SET) process and not via the typical SNAr mechanism. This method differs from the previously reported nickel/copper-cocatalyzed system in terms of scope of the substrate and has exhibited good scalability. Double and triple ipso-borylations of several di- and trifluoroarenes have been also achieved efficiently, enhancing the synthetic utility of this method.

Ni/Cu-Catalyzed Defluoroborylation of Fluoroarenes for Diverse C-F Bond Functionalizations

Ni/Cu-catalyzed transformation of fluoroarenes to arylboronic acid pinacol esters via C-F bond cleavage has been achieved. Further versatile derivatization of an arylboronic ester has allowed for the facile two-step conversion of a fluoroarene to diverse functionalized arenes, demonstrating the synthetic utility of the method.

Synthesis of trimethylstannyl arylboronate compounds by sandmeyer-type transformations and their applications in chemoselective cross-coupling reactions

A synthetic method based on Sandmeyer-type reactions to access both tin- and boron-substituted arenes from nitroaniline derivatives is described. This transformation can be applied to the synthesis of a series of functionalized trimethylstannyl arylboronates. In addition, the chemoselective reaction of the Stille and Suzuki-Miyaura cross-coupling reactions is explored, and a series of m- and p-terphenyl derivatives have been synthesized by conducting consecutive one-pot Stille and Suzuki-Miyaura cross-coupling reactions.