223799-24-4

Usage

Type of compound

Boron-containing heterocyclic compound

Usage

Commonly used in organic synthesis and medicinal chemistry

Ability

Valued for its ability to form carbon-carbon bonds

Reagent

Often used in Suzuki-Miyaura coupling reactions

Building block

Used in the synthesis of pharmaceuticals and agrochemicals

Reaction conditions

Mild reaction conditions

Functional group tolerance

High functional group tolerance, making it a versatile tool for the construction of complex organic molecules.

Upstream product

• 668987-38-0 5,5-dimethyl-1,3,2-dioxaborinane 
• 1077-02-7 3-methylphenyl methanesulfonate 
• 3955-72-4 3-methylphenyl tosylate 
• 17933-03-8 m-tolylboronic acid 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 28987-79-3 m-tolylmagnesium bromide 
• 4250-47-9 (3-CH₃-C₆H₄)BCl₂ 
• 5097-06-3 3,3'-sulfinylbis(methylbenzene) 
• 201733-56-4 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane 

Downstream Products

• 1060639-06-6 1,4,5,8-tetrakis(3-methylphenyl)-9,10-anthracenedione 
• 14625-58-2 2-(3-methylphenyl)benzoxazole 
• 1329491-64-6 2-[(3'-methylbiphenyl-2-yl)sulfinyl]pyridine 
• 643-93-6 3-methylbiphenyl 
• 1356399-82-0 1-(3-methylphenyl)-1-(naphthalen-2-yl)ethanol 
• 198648-99-6 tert-butyl 4-hydroxy-4-(3-methylphenyl)-1-piperidinecarboxylate 
• 6957-08-0 1-(m-Methylphenyl)cyclohexanol 
• 1510828-54-2 2-phenyl-6-(m-tolyl)pyridine 
• 4373-61-9 2-(m-tolyl)pyridine 
• 1010720-56-5 1-(2,2-difluoro-1-phenylvinyl)-3-methylbenzene 
• 36821-15-5 2-(3-methylphenyl)naphthalene 

Relevant academic research and scientific papers

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.

Ruthenium-Catalyzed C-H Arylation and Alkenylation of Furfural Imines with Boronates

A Ru0-catalyzed direct C-H arylation and alkenylation of furfural imines with aryl- or alkenyl-boronates, in the presence of benzylideneacetone as a sacrificial hydride acceptor, is disclosed. This reaction provides access, after hydrolysis, to C3-arylated or vinylated furfural derivatives, and thus valorizes these relevant building-blocks obtained from lignocellulosic biomass. This approach, involving C-H activation by a Ru0/RuII, cycle offers several advantages, notably simple, mild and neutral reaction conditions.

Palladium-catalysed reactions of conjugated enyne oxiranes with organoborons: A diastereoselective method of the synthesis of 2,4,5-trienol derivatives

A palladium-catalysed reaction of conjugated enyne oxiranes with organoboron reagents is described. This method allows aryl-substituted vinylallenes containing a hydroxyl group on the allylic position to be synthesized, with good diastereomeric ratios, un

Ruthenium-Catalyzed Ortho C-H Arylation of Aromatic Nitriles with Arylboronates and Observation of Partial Para Arylation

Ruthenium-catalyzed C-H arylation of aromatic nitriles with arylboronates is described. The use of RuH2(CO){P(4-MeC6H4)3}3 as a catalyst provided higher yields of the ortho arylation products than the

Selective Monoarylation of Aromatic Ketones and Esters via Cleavage of Aromatic Carbon-Heteroatom Bonds by Trialkylphosphine Ruthenium Catalysts

We report here the ruthenium-catalyzed selective monoarylation of aromatic ketones bearing two ortho carbon-heteroatom (O or N) bonds. Under the newly developed catalyst system consisting of RuHCl(CO)(PiPr3)2, CsF, and sty

Syntheses of RuHCl(CO)(PAr3)3 and RuH2(CO)(PAr3)3 Containing various triarylphosphines and their use for arylation of sterically congested aromatic C-H bonds

A series of ruthenium complexes, RuHCl(CO)(PAr3)3 and RuH2(CO)(PAr3)3, containing various triarylphosphines were synthesized. Screening of these complexes as catalysts for direct arylation of sterically congested ortho C-H bonds of aromatic ketones improved the yields of the arylation products.

Synthesis of arylboronates by boron-induced ipso-deantimonation of triarylstibanes with boron trihalides and its application in one-pot two-step transmetallation/cross-coupling reactions

The reaction of triarylstibanes (1) with boron trihalides (BCl3, and BBr3) afforded arylboron dihalides (2) by utilizing all the three aryl groups on the antimony. Boron intermediates (2) were transformed to arylboronates (3) in good to excellent yields by treatment with methanol and 1,3-propanediol. Further, the Pd-catalyzed reactions of 2 with organic halides such as 1-bromonaphthalene and benzoyl chloride in the presence of H2O afforded the corresponding cross-coupling products, unsymmetrical biaryls (4) and ketones (5), in moderate to good yields. The potential energy surfaces for the transmetallations of triarylstibanes (1) with BCl3 affording 2 were determined by molecular orbital calculations. The analyses of substituent effects on theoretically calculated reactivities showed the importance of the resonance effects of the ring substituents on these transmetallations.

Synthesis of enantiomerically enriched triarylmethanes by enantiospecific suzuki-miyaura cross-coupling reactions

The Suzuki-Miyaura cross-coupling of chiral, enantiomerically enriched dibenzylic boronic esters is described. The reaction proceeds with almost complete retention of stereochemistry, providing access to triarylmethanes, compounds that have high biologica

SYNTHESIS OF BORONIC ESTERS AND BORONIC ACIDS USING GRIGNARD REAGENTS

Boronic esters and boronic acids are synthesized at ambient temperature in an ethereal solvent by the reaction of Grignard reagents with a boron-containing substrate. The boron-containing substrate may be a boronic ester such as pinacolborane, neopentylglycolborane, or a dialkylaminoborane compound such as diisopropylaminoborane. The Grignard reagents may be preformed or generated from an alkyl, alkenyl, aryl, arylalkyl, heteroaryl, vinyl, or allyl halide compound and Mg°. When the boron-containing substrate is a boronic ester, the reactions generally proceed at room temperature without added base in about 1 to 3 hours to form a boronic ester compound. When the boron-containing substrate is a dialkylaminoborane compound, the reactions generally proceed to completion at 0°C in about 1 hour to form a boronic acid compound.

Ni-catalysed, domino synthesis of tertiary alcohols from secondary alcohols

The use of in situ generated (NHC)-Ni catalytic species (NHC = N-heterocyclic carbene) allows for the synthesis, in short reaction times, of a variety of tertiary alcohols from secondary alcohols through a domino oxidation-addition protocol.