5123-05-7

Usage

Chemical class

Dioxaborinane derivative
It belongs to a class of organic compounds containing a dioxaborinane ring.

Structure

Consists of a dioxaborinane ring, a 1,1'-biphenyl group, and 5,5-dimethyl substitutions
The compound has a unique structure that contributes to its stability and reactivity.

Stability

Known for its stability
The compound is stable and can be used in various chemical reactions without decomposing easily.

Compatibility

Compatible with a wide range of functional groups
It can be used in reactions with various functional groups, making it a versatile reagent in organic chemistry.

Applications

Used in organic synthesis for the production of pharmaceuticals, agrochemicals, and materials
The compound serves as a building block for creating a variety of useful products.

Interest in development

Subject of interest in the development of new catalysts and materials
Its unique structure and properties make it a promising candidate for the development of novel catalysts and materials.

Reactivity

Valuable reagent in organic chemistry
Due to its stability and compatibility with various functional groups, it is a valuable reagent for use in organic chemistry.

Upstream product

• 5122-94-1 4-biphenylboronic acid 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 92-66-0 4-bromo-1,1'-biphenyl 
• 201733-56-4 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane 
• 92-92-2 biphenyl-4-carboxylic acid 
• 78322-97-1 phenyl [1,1′-biphenyl]-4-carboxylate 
• 14002-51-8 4-biphenyl-carboxylic acid chloride 
• 169963-54-6 4-(morpholino)biphenyl 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 574755-28-5 (4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)trimethylsilane 
• 17865-11-1 (4-(trimethylsilyl)phenyl)boronic acid 
• 91815-47-3 4,4″-sulfinyldi-1,1′-biphenyl 
• 613-37-6 4-methoxylbiphenyl 
• 16881-71-3 4'-methoxy-1,1'-biphenyl-4-ol 

Downstream Products

• 479417-35-1 4,4'-di(biphenyl)-2,2'-bipyridine 
• 92-92-2 biphenyl-4-carboxylic acid 
• 125643-81-4 2-biphenyl-4-yl-1,1-diphenyl-ethene 
• 1435463-60-7 C₁₈H₁₅BO 
• 1435463-74-3 2-([1,1'-biphenyl]-4-yl)-2-phenyl-1,3,2-oxazaborolidin-3-ium-2-uide 
• 112321-79-6 2-([1,1'-biphenyl]-4-yl)-6-phenylpyridine 
• 93324-66-4 2-(4-phenylphenyl)pyridine 
• 92-94-4 [1,1';4',1'']terphenyl 
• 68862-02-2 2-([1,1'-biphenyl]-4-yl)naphthalene 
• 177551-63-2 [1,1′-biphenyl]-4-yl(trifluoromethyl)sulfane 
• 720-75-2 methyl 4-phenylbenzoate 

Relevant academic research and scientific papers

Cobalt-Catalyzed C(sp2)-C(sp3) Suzuki-Miyaura Cross Coupling

A cobalt-catalyzed method for the C(sp2)-C(sp3) Suzuki-Miyaura cross coupling of aryl boronic esters and alkyl bromides is described. Cobalt-ligand combinations were assayed with high-throughput experimentation, and cobalt(II) sources with trans-N,N′-dimethylcyclohexane-1,2-diamine (DMCyDA, L1) produced optimal yield and selectivity. The scope of this transformation encompassed steric and electronic diversity on the aryl boronate nucleophile as well as various levels of branching and synthetically valuable functionality on the electrophile. Radical trap experiments support the formation of electrophile-derived radicals during catalysis.

Selective C-O Bond Reduction and Borylation of Aryl Ethers Catalyzed by a Rhodium-Aluminum Heterobimetallic Complex

We report the catalytic reduction of a C-O bond and the borylation by a rhodium complex bearing an X-Type PAlP pincer ligand. We have revealed the reaction mechanism based on the characterization of the reaction intermediate and deuterium-labeling experiments. Notably, this novel catalytic system shows steric-hindrance-dependent chemoselectivity that is distinct from conventional Ni-based catalysts and suggests a new strategy for selective C-O bond activation by heterobimetallic catalysis.

Ni-Catalyzed Borylation of Aryl Sulfoxides

A nickel/N-heterocyclic carbene (NHC) catalytic system has been developed for the borylation of aryl sulfoxides with B2(neop)2 (neop=neopentyl glycolato). A wide range of aryl sulfoxides with different electronic and steric properties were converted into the corresponding arylboronic esters in good yields. The regioselective borylation of unsymmetric diaryl sulfoxides was also feasible leading to borylation of the sterically less encumbered aryl substituent. Competition experiments demonstrated that an electron-deficient aryl moiety reacts preferentially. The origin of the selectivity in the Ni-catalyzed borylation of electronically biased unsymmetrical diaryl sulfoxide lies in the oxidative addition step of the catalytic cycle, as oxidative addition of methoxyphenyl 4-(trifluoromethyl)phenyl sulfoxide to the Ni(0) complex occurs selectively to give the structurally characterized complex trans-[Ni(ICy)2(4-CF3-C6H4){(SO)-4-MeO-C6H4}] 4. For complex 5, the isomer trans-[Ni(ICy)2(C6H5)(OSC6H5)] 5-I was structurally characterized in which the phenyl sulfinyl ligand is bound via the oxygen atom to nickel. In solution, the complex trans-[Ni(ICy)2(C6H5)(OSC6H5)] 5-I is in equilibrium with the S-bonded isomer trans-[Ni(ICy)2(C6H5)(SOC6H5)] 5, as shown by NMR spectroscopy. DFT calculations reveal that these isomers are separated by a mere 0.3 kJ/mol (M06/def2-TZVP-level of theory) and connected via a transition state trans-[Ni(ICy)2(C6H5)(η2-{SO}-C6H5)], which lies only 10.8 kcal/mol above 5.

Transition-Metal-Free ipso-Trifluoromethylthiolation of Lithium Aryl Boronates

A transition-metal-free direct trifluoromethylthiolation of the ipso-carbon of lithium aryl boronates with trifluoromethanesulfenate under mild conditions was described. In addition, late-stage site-selective C-H borylation/trifluoromethylation and C-Cl b

Mechanism and Scope of Nickel-Catalyzed Decarbonylative Borylation of Carboxylic Acid Fluorides

This Article describes the development of a base-free, nickel-catalyzed decarbonylative coupling of carboxylic acid fluorides with diboron reagents to selectively afford aryl boronate ester products. Detailed studies were conducted to assess the relative rates of direct transmetalation between aryl boronate esters and diboron reagents and a bisphosphine nickel(aryl)(fluoride) intermediate. These investigations revealed that diboron reagents undergo transmetalation with this Ni(aryl)(fluoride) intermediate at rates significantly faster than their aryl boronate ester congeners. Furthermore, the reactivity of both boron reagents toward transmetalation is enhanced with increasing electrophilicity of the boron center. These mechanistic insights were leveraged to develop a catalytic decarbonylative borylation of acid fluorides that proved applicable to a variety of (hetero)aryl carboxylic acid fluorides as well as diverse diboron reagents. The acid fluorides can be generated in situ directly from carboxylic acids. Furthermore, the mechanistic studies directed the identification of various air-stable Ni pre-catalysts for this transformation.

Copper-catalysed borylation of aryl chlorides

We report herein the first Cu-catalysed borylation of a wide range of aryl chlorides with different electronic and steric properties using a readily prepared NHC-stabilised Cu catalyst and KOtBu as the base with B2pin2 (pin = pinacolato) as the boron reagent. The aryl chlorides are converted into their corresponding arylboronic esters in good yields. The new procedure shows broad functional group tolerance, and B2neop2 (neop = neopentyl glycolato) can also be applied as the boron reagent.

Direct Borylation of Tertiary Anilines via C-N Bond Activation

The first successful catalytic borylation of unactivated aromatic C-N bonds of tertiary anilines without the preactivation or any directing groups is demonstrated. The reactivity of both N,N-dialkylarylamines and N-arylpyrroles were investigated systematically, and the targeted products were furnished in moderate to good yields. The DFT calculation results indicated that the catalytic cycle is furnished via a five-membered cyclic transition-state due to the steric hindrance of the Ni/NHC catalytic system.

Light-Induced Gold-Catalyzed Hiyama Arylation: A Coupling Access to Biarylboronates

Organoboron compounds are versatile synthetic building blocks. We herein report a new strategy, a photochemical gold-catalyzed chemo-selective Hiyama arylation of B,Si bifunctionalized reagents with diazonium salts, which is orthogonal to common strategies and therefore a unique tool for synthesis of valuable biarylboronates. With this new methodology a wide array of diversely functionalized sp2- and sp3-hybridized biarylboronates were obtained. Notably, the synergism of gold catalysis with copper catalysis or palladium catalysis, allows for one-pot iterative C?X (heteroatom) and C?C couplings for the rapid assembly of several simple fragments to relatively complex molecules. Mechanistic studies indicated that photosensitizer-free conditions were superior to gold/Ru(bpy)3Cl2 dual catalysis.

Rhodium-Catalyzed Decarbonylative Borylation of Aromatic Thioesters for Facile Diversification of Aromatic Carboxylic Acids

Transformation of aromatic thioesters into arylboronic esters was achieved efficiently using a rhodium catalyst. The broad functional-group tolerance and mild conditions of the method have allowed for the two-step decarboxylative borylation of a wide range of aromatic carboxylic acids, including commercially available drugs.

Direct Access to α,α-Difluoroacylated Arenes by Palladium-Catalyzed Carbonylation of (Hetero)Aryl Boronic Acid Derivatives

A palladium-catalyzed carbonylative coupling of (hetero)aryl boronates or boronic acid salts with carbon monoxide and α-bromo-α,α-difluoroamides and bromo-α,α-difluoroesters is described herein. The method is useful for the synthesis of a diverse selection of (hetero)aryl α,α-difluoro-β-ketoamides and α,α-difluoro-β-ketoesters, which are useful building blocks for the generation of functionalized difluoroacylated and difluoroalkyl arenes. The method could be further extended to a one-pot protocol for the formation of difluoroacetophenones.