Category: 214360-44-8

Kita, Yusuke published the artcileRhodium-catalyzed carbon-cyano bond cleavage reactions using organosilicon reagents, SDS of cas: 214360-44-8, the publication is Yuki Gosei Kagaku Kyokaishi (2010), 68(11), 1112-1122, database is CAplus.

Rh-catalyzed C-cyano bond cleavage reactions using organosilicon reagents are described. When disilane is used as the Si reagent, the C-CN bonds in aryl and alkenyl cyanides are silylated to form the corresponding silylated products along with silyl cyanide. Reductive decyanation of nitriles is achieved when hydrosilane is used as the Si reagent. This catalytic system can be applied to the C(sp³)-CN bonds in simple aliphatic nitriles. In both reactions, the silylrhodium species generated in situ serves as a catalytically active species, cleaving C-CN bonds via an η²-iminoacyl complex. Addition of external electrophiles allowed the Si-assisted cleavage of C-CN bonds to be applied to C-C bond formation reactions. Intramol. arylation of benzonitrile bearing a tethered chlorophenyl group and decyanative Mizoroki-Heck-type alkenylation of nitriles with vinylsilanes have been developed.

Yuki Gosei Kagaku Kyokaishi published new progress about 214360-44-8. 214360-44-8 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Boronic acid and ester,Benzene,Boronic Acids,Boronic acid and ester, name is 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, and the molecular formula is C12H14BNO2, SDS of cas: 214360-44-8.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Peschiulli, Aldo published the artcileRuthenium-Catalyzed α-(Hetero)Arylation of Saturated Cyclic Amines: Reaction Scope and Mechanism, Recommanded Product: 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, the publication is Chemistry – A European Journal (2013), 19(31), 10378-10387, database is CAplus and MEDLINE.

Transition-metal-catalyzed sp³ C-H activation has emerged as a powerful approach to functionalize saturated cyclic amines. Our group recently disclosed a direct catalytic arylation reaction of piperidines at the α position to the nitrogen atom. 1-(Pyridin-2-yl)piperidine could be smoothly α-arylated if treated with an arylboronic ester in the presence of a catalytic amount of [Ru₃(CO)₁₂] and one equivalent of 3-ethyl-3-pentanol. A systematic study on the substrate and reagent scope of this transformation is disclosed in this paper. The effect of substitution on both the piperidine ring and the arylboronic ester has been investigated. Smaller (pyrrolidine) and larger (azepane) saturated ring systems, as well as benzoannulated derivatives, were found to be compatible substrates with the α-arylation protocol. The successful use of a variety of heteroarylboronic esters as coupling partners further proved the power of this direct functionalization method. Mechanistic studies have allowed for a better understanding of the catalytic cycle of this remarkable transformation featuring an unprecedented direct transmetalation on a Ru^II-H species.

Chemistry – A European Journal published new progress about 214360-44-8. 214360-44-8 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Boronic acid and ester,Benzene,Boronic Acids,Boronic acid and ester, name is 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, and the molecular formula is C12H14BNO2, Recommanded Product: 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Ludwig, Jacob R. published the artcileCobalt-Catalyzed C(sp²)-C(sp³) Suzuki-Miyaura Cross Coupling, Recommanded Product: 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, the publication is Organic Letters (2021), 23(3), 625-630, database is CAplus and MEDLINE.

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.

Organic Letters published new progress about 214360-44-8. 214360-44-8 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Boronic acid and ester,Benzene,Boronic Acids,Boronic acid and ester, name is 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, and the molecular formula is C12H14BNO2, Recommanded Product: 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Kikushima, Kotaro published the artcileCopper-mediated one-pot synthesis of trifluorostyrene derivatives from tetrafluoroethylene and arylboronate, Quality Control of 214360-44-8, the publication is Chemistry Letters (2015), 44(7), 1019-1021, database is CAplus.

The copper-mediated synthesis of trifluorostyrenes ArCF:CF₂ (Ar = C₆H₅, 4-MeOC₆H₄, 2-naphthyl, etc.) from aryl boronates and tetrafluoroethylene through the transmetalation-carbocupration-β-fluorine elimination process under one-pot procedure was described. β-Fluorine elimination of a 2-aryl-1,1,2,2-tetrafluoroethylcopper complex, generated in situ from arylboronate, copper tert-butoxide, and 1,10-phenanthroline/bathophenanthroline with tetrafluoroethylene via carbocupration, was promoted by the addition of a Lewis acid.

Chemistry Letters published new progress about 214360-44-8. 214360-44-8 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Boronic acid and ester,Benzene,Boronic Acids,Boronic acid and ester, name is 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, and the molecular formula is C12H14BNO2, Quality Control of 214360-44-8.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Ohashi, Masato published the artcilePalladium-catalyzed base-free Suzuki-Miyaura coupling reactions of fluorinated alkenes and arenes via a palladium fluoride key intermediate, Product Details of C12H14BNO2, the publication is European Journal of Organic Chemistry (2013), 2013(3), 443-447, database is CAplus.

A new strategy for C-C bond formation with organoboronates through C-F activation of fluorinated alkenes and arenes was developed. In this Pd-catalyzed Suzuki-Miyaura-type cross-coupling reaction, neither a base for enhancing the reactivity of the organoboron reagents nor a Lewis acid for promoting C-F bond activation was required. A fluoro-palladium intermediate played an essential role in this reaction. In addition, a Ni(NHC) catalyst was efficient for C-C coupling through C-F bond activation of fluoroarenes.

European Journal of Organic Chemistry published new progress about 214360-44-8. 214360-44-8 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Boronic acid and ester,Benzene,Boronic Acids,Boronic acid and ester, name is 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, and the molecular formula is C12H14BNO2, Product Details of C12H14BNO2.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Mailig, Melrose published the artcilePractical catalytic method for synthesis of sterically hindered anilines, Quality Control of 214360-44-8, the publication is Chemical Communications (Cambridge, United Kingdom) (2015), 51(55), 11048-11051, database is CAplus and MEDLINE.

A practical catalytic method for the synthesis of sterically hindered anilines is described. The amination of aryl and heteroaryl boronic esters is accomplished using a catalyst prepared in situ from com. available and air-stable copper(I) triflate and a diphosphine ligand. For the first time, the method can be applied to the synthesis of both secondary and tertiary anilines in the presence of a wide range of functional groups. Esters, aldehydes, alcs., aryl halides, ketones, nitriles and nitro arenes are all compatible with the reaction conditions. Finally, even the most sterically hindered anilines can be successfully prepared under mild reaction conditions. Overall, the new method addresses significant practical limitations of a transformation previously developed and provides a valuable complement to the existing methods for the synthesis of anilines. Under optimized conditions the synthesis of the target compounds was achieved using 1,1′-(oxydi-2,1-phenylene)bis[1,1-dicyclohexylphosphine] (i.e. phosphine-ether) and copper(I) triflate compound with benzene (2:1) as ligand-catalyst combination. Starting materials included N-(benzoyloxy)-N-(1-methylethyl)-2-propanamine (hydroxylamine derivative), benzoic acid 1-pyrrolidinyl ester, 4-(benzoyloxy)-1-piperazinecarboxylic acid 1,1-dimethylethyl ester, benzoic acid 4-morpholinyl ester, benzoic acid 4-hydroxy-1-piperidinyl ester, benzoic acid 2,2,6,6-tetramethyl-1-piperidinyl ester. Boronic acid cyclic esters included 5,5-dimethyl-2-(2-methylphenyl)-1,3,2-dioxaborinane, 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzoic acid ester, 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzaldehyde, 2-chloro-3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)pyridine, 5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)pyrimidine, 5,5-dimethyl-2-(3-thienyl)-1,3,2-dioxaborinane (thiophene derivative). The title compounds thus formed included 4-bromo-N,N-bis(1-methylethyl)benzenamine (tertiary amine, tertiary aniline), 2,6-dimethyl-N-(1-methylethyl)benzenamine (secondary amine, secondary aniline). The reaction of a [1,1′-(oxydi-2,1-phenylene)bis[1,1-dicyclohexylphosphine-.kappa .P]]copper complex intermediate with N-(benzoyloxy)-2-methyl-2-propanamine was reported.

Chemical Communications (Cambridge, United Kingdom) published new progress about 214360-44-8. 214360-44-8 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Boronic acid and ester,Benzene,Boronic Acids,Boronic acid and ester, name is 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, and the molecular formula is C12H14BNO2, Quality Control of 214360-44-8.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Li, Gen published the artcileP(III)/P(V)-Catalyzed Methylamination of Arylboronic Acids and Esters: Reductive C-N Coupling with Nitromethane as a Methylamine Surrogate, Synthetic Route of 214360-44-8, the publication is Journal of the American Chemical Society (2020), 142(38), 16205-16210, database is CAplus and MEDLINE.

The direct reductive N-arylation of nitromethane by organophosphorus-catalyzed reductive C-N coupling with arylboronic acid derivatives is reported. This method operates by the action of a small ring organophosphorus-based catalyst (1,2,2,3,4,4-hexamethylphosphetane P-oxide) together with a mild terminal reductant hydrosilane to drive the selective installation of the methylamino group to (hetero)aromatic boronic acids and esters. This method also provides for a unified synthetic approach to isotopically labeled N-methylanilines from various stable isotopologues of nitromethane (i.e., CD₃NO₂, CH₃¹⁵NO₂, and ¹³CH₃NO₂), revealing this easy-to-handle compound as a versatile precursor for the direct installation of the methylamino group.

Journal of the American Chemical Society published new progress about 214360-44-8. 214360-44-8 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Boronic acid and ester,Benzene,Boronic Acids,Boronic acid and ester, name is 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, and the molecular formula is C12H14BNO2, Synthetic Route of 214360-44-8.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Perez-Garcia, Raul M. published the artcileMild, organo-catalysed borono-deamination as a key to late-stage pharmaceutical precursors and ¹⁸F-labelled radiotracers, Synthetic Route of 214360-44-8, the publication is Frontiers in Chemistry (Lausanne, Switzerland) (2022), 884478, database is CAplus and MEDLINE.

A tris(pentafluorophenyl)borane catalyzed method for the synthesis of boronic acid esters from aromatic amines in yields of up to 93% was devised. Mild conditions, benign reagents, short reaction times, low temperatures and a wide substrate scope characterize the method. The reaction was found applicable to the synthesis of boronic acid ester derivatives of complex drug mols. in up to 86% isolated yield and high purity suitable for labeling. These boronates were subsequently labeled with [18F] fluoride ion in radiochem. yields of up to 55% with and even without isolation of the boronate-intermediate.

Frontiers in Chemistry (Lausanne, Switzerland) published new progress about 214360-44-8. 214360-44-8 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Boronic acid and ester,Benzene,Boronic Acids,Boronic acid and ester, name is 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, and the molecular formula is C12H14BNO2, Synthetic Route of 214360-44-8.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Leowanawat, Pawaret published the artcileZero-Valent Metals Accelerate the Neopentylglycolborylation of Aryl Halides Catalyzed by NiCl₂-Based Mixed-Ligand Systems, Application In Synthesis of 214360-44-8, the publication is Journal of Organic Chemistry (2010), 75(22), 7822-7828, database is CAplus and MEDLINE.

The highly active mixed-ligand catalytic system NiCl₂(dppp)/dppf combined with the reducing effect of zerovalent Zn and of other metals was used to demonstrate a method for the dramatic acceleration of the rate and for the enhancement of the yield of Ni-catalyzed neopentylglycolborylation of aryl halides. A diversity of electron-rich and electron-deficient aryl iodides, bromides, and chlorides were efficiently neopentylglycolborylated, typically in 1 h or less. This acceleration is particularly remarkable for the generally less reactive aryl bromides and chlorides and for all ortho-substituted aryl halides. By accelerating the rate of borylation and reducing its reaction time to complete conversion, pathways leading to protodeborylated or hydrodehalogenated side products have a reduced impact on the outcome of the overall reaction. Although Zn powder was the reducing agent of choice, compatibility of this technique with more readily recoverable Zn chips, as well as other metals such as Mn, Mg, Fe, Al, and Ca, demonstrated the broad scope of this synthetic method.

Journal of Organic Chemistry published new progress about 214360-44-8. 214360-44-8 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Boronic acid and ester,Benzene,Boronic Acids,Boronic acid and ester, name is 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, and the molecular formula is C12H14BNO2, Application In Synthesis of 214360-44-8.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Ohishi, Takeshi published the artcileCarboxylation of organoboronic esters catalyzed by N-heterocyclic carbene copper(I) complexes, Synthetic Route of 214360-44-8, the publication is Angewandte Chemie, International Edition (2008), 47(31), 5792-5795, database is CAplus and MEDLINE.

N-heterocyclic carbene copper(I) complexes serve as excellent catalysts for the carboxylation of aryl- and alkenylboronic esters with CO₂, affording a variety of functionalized carboxylic acid derivatives Important active intermediates such as the copper(I) aryl and carboxylate complexes, [(IPr)CuR] and [(IPr)CuOCOR] (R = 4-MeOC₆H₄, IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene), are isolated and structurally characterized.

Angewandte Chemie, International Edition published new progress about 214360-44-8. 214360-44-8 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Boronic acid and ester,Benzene,Boronic Acids,Boronic acid and ester, name is 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, and the molecular formula is C12H14BNO2, Synthetic Route of 214360-44-8.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts