820223-94-7

Usage

Uses

Used in Organic Synthesis:
2-(4-Cyclohexylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is used as a reagent in organic synthesis for its ability to form carbon-carbon bonds through the Suzuki-Miyaura cross-coupling reaction. This reaction is a widely used method in the synthesis of various organic compounds, including pharmaceuticals and materials.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 2-(4-Cyclohexylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is used as a building block for the synthesis of complex organic molecules with potential therapeutic applications. Its unique structure and reactivity allow for the creation of diverse molecular structures with specific biological activities.
Used in Materials Chemistry:
2-(4-Cyclohexylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is also utilized in materials chemistry as a component in the development of new materials with unique properties. Its versatility in forming carbon-carbon bonds enables the synthesis of materials with tailored characteristics for various applications, such as electronics, energy storage, and advanced materials.

Upstream product

• 25109-28-8 4-bromo(cyclohexyl)benzene 
• 73183-34-3 bis(pinacol)diborane 
• 68716-49-4 p-bromophenylboronic acid pinacol ester 
• 827-52-1 1-phenyl-1-cyclohexane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 1131-60-8 p-cyclohexylphenol 
• 110-82-7 cyclohexane 

Downstream Products

• 374538-04-2 (4-cyclohexylphenyl)boronic acid 

Relevant academic research and scientific papers

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

Dealkenylative Ni-Catalyzed Cross-Coupling Enabled by Tetrazine and Photoexcitation

A new and general method to functionalize the C(sp3)-C(sp2) bond of alkyl and alkene linkages has been developed, leading to the dealkenylative generation of carbon-centered radicals that can be intercepted to undergo Ni-catalyzed C(sp3)-C(sp2) cross-coupling. This one-pot protocol leverages the easily procured alkene feedstocks for organic synthesis with excellent functional group compatibility without the need for a photoredox catalyst.

Oxazole or thiazole compound and organic electroluminescent device thereof

The invention provides an oxazole or thiazole compound and an organic electroluminescent device thereof. Belong to organic electroluminescence technical field. The oxazole or thiazole compound provided by the invention has a proper HOMO energy level, can

Rapid and Direct Photocatalytic C(sp3)?H Acylation and Arylation in Flow

Herein, we report a photocatalytic procedure that enables the acylation/arylation of unfunctionalized alkyl derivatives in flow. The method exploits the ability of the decatungstate anion to act as a hydrogen atom abstractor and produce nucleophilic carbon-centered radicals that are intercepted by a nickel catalyst to ultimately forge C(sp3)?C(sp2) bonds. Owing to the intensified conditions in flow, the reaction time can be reduced from 12–48 hours to only 5–15 minutes. Finally, kinetic measurements highlight how the intensified conditions do not change the reaction mechanism but reliably speed up the overall process.

Development and Mechanistic Studies of Iron-Catalyzed Construction of Csp2-B Bonds via C-O Bond Activation

Herein we describe an iron-catalyzed borylation of alkenyl and aryl carbamates through the activation of a C-O bond. This protocol exhibits high efficiency, a broad substrate scope, and the late-stage borylation of biorelevant compounds, thus providing potential applications in medicinal chemistry. Moreover, this method enables orthogonal transformations of phenol derivatives and also offers good opportunities for the synthesis of multisubstituted arenes. Preliminary mechanistic studies suggest that a FeII/FeIII catalytic cycle via a radical pathway might be involved in the reaction.

Iron-Catalyzed Borylation of Aryl Ethers via Cleavage of C-O Bonds

Herein, we report the iron-catalyzed borylation of aryl ethers and aryl amines via cleavage of C-O and C-N bonds. This protocol does not require the use of Grignard reagents and displays a broad substrate scope, which allows the late-stage borylation. It also provides facile access to multisubstituted arenes through C-H functionalization using 2-pyridyloxy as the directing group.

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.

Pd-Catalyzed Site-Selective Borylation of Simple Arenes via Thianthrenation?

Site-selective borylation of simple arenes was realized in one pot via an electrophilic thianthrenation/Pd-catalyzed borylation sequence. The key to achieve this operatically simple process is the use of Pd catalysis, which could tolerate the solvent and acidic conditions used in the thianthrenation step. This protocol features mild conditions, broad functional group tolerance, and simple manipulations, and is suitable for late-stage functionalization of a wide range of pharmaceuticals and complex bioactive molecules.

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.

C(sp3)-C(sp2) cross-coupling of alkylsilicates with borylated aryl bromides-an iterative platform to alkylated aryl- and heteroaryl boronates

The attractive field of iterative cross-coupling has seen numerous advances, although almost exclusively in the union of sp2-hybridized partners. Conspicuously absent from this useful synthetic manifold is the inclusion of sp3-hybridized pronucleophiles that can undergo transmetalation under mild conditions. Described here is the use of primary and secondary ammonium alkylsilicates, which undergo facile C(sp3)-C(sp2) cross-coupling with borylated aryl bromide partners under photoredox/nickel dual catalysis conditions. This operationally simple procedure allows the production of alkylated small molecules possessing boronate ester (BPin, Bneopentyl, BMIDA) functional handles. Because of the extremely mild reaction conditions and the innocuous byproduct generated upon fragmentative oxidation of silicates, the corresponding borylated compounds were isolated in good to excellent yields. Aryl bromides bearing unprotected boronic acids are also generally tolerated for the first time and prove useful in multistep syntheses. Unlike many previously reported photoredox/Ni dual cross-couplings, the C(sp3)-C(sp2) bonds were forged using a transition metal-free photocatalyst, allowing a substantial increase in sustainability as well as a cost reduction. Because the developed Ni-catalyzed cross-coupling does not require discrete boron speciation control, as in many popular orthogonal Pd-based methods, this protocol represents a significant advance in atom- and step-economy.