Tag: M.W=200-250

Wilson, Daniela A. published the artcileNeopentylglycolborylation of Aryl Mesylates and Tosylates Catalyzed by Ni-Based Mixed-Ligand Systems Activated with Zn, Formula: C12H14BNO2, the publication is Journal of the American Chemical Society (2010), 132(6), 1800-1801, database is CAplus and MEDLINE.

The mixed-ligand system NiCl₂(dppp)/dppf is shown to be an effective catalyst for the neopentylglycolborylation of ortho-, meta-, and para-substituted electron-rich and electron-deficient aryl mesylates and tosylates. The addition of Zn powder as a reductant dramatically increases the reaction yield and reduces the reaction time by more than an order of magnitude, providing complete conversion in 1-3 h.

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 C10H9ClN2O, Formula: C12H14BNO2.

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

Moldoveanu, Costel published the artcileNeopentylglycolborylation of Aryl Chlorides Catalyzed by the Mixed Ligand System NiCl₂(dppp)/dppf, SDS of cas: 214360-44-8, the publication is Organic Letters (2009), 11(21), 4974-4977, database is CAplus and MEDLINE.

The mixed ligand system 10 mol % NiCl₂(dppp) with 5 mol % dppf was discovered to be an extremely efficient catalyst for the neopentylglycolborylation of a diversity of electron-rich and electron-deficient aryl chlorides. Optimization showed that 5 mol % catalyst with 10% dppf was even more efficient. These results highlight the complexity of the relation between catalyst and coligand in Ni catalysis and the benefit of combinations of mixed ligand in catalyst design.

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, SDS of cas: 214360-44-8.

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

Yang, Bowen published the artcileDiscovery of a series of 1H-pyrrolo[2,3-b]pyridine compounds as potent TNIK inhibitors, HPLC of Formula: 1036991-35-1, the publication is Bioorganic & Medicinal Chemistry Letters (2021), 127749, database is CAplus and MEDLINE.

In an inhouse screening, 1H-pyrrolo[2,3-b]pyridine scaffold was found to have high inhibition on TNIK. Several series of compounds were designed and synthesized, among which some compounds had potent TNIK inhibition with IC₅₀ values lower than 1 nM. Some compounds showed concentration-dependent characteristics of IL-2 inhibition. These results provided new applications of TNIK inhibitors and new prospects of TNIK as a drug target.

Bioorganic & Medicinal Chemistry Letters published new progress about 1036991-35-1. 1036991-35-1 belongs to nitriles-buliding-blocks, auxiliary class Boronic acid and ester,Boronic Acids,Boronate Esters, name is 3-Amino-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile, and the molecular formula is C14H12N2S, HPLC of Formula: 1036991-35-1.

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

Razafindrainibe, Franck published the artcileSonogashira Cross-Coupling Reaction of Bromocyanofluoro Pyridine Compounds: Access to 5- and 6-Alkynylfluoropyridinamidoximes Scaffolds, Quality Control of 1256788-71-2, the publication is European Journal of Organic Chemistry (2021), 2021(30), 4393-4397, database is CAplus.

A general two-step procedure to access hitherto unknown and under explored 5- and 6-alkynyl-3-fluoro-2-pyridinamidoximes I [R = 4-EtC₆H₄, 3-pyridyl, tridecyl, etc.; R¹ = (N’-hydroxycarbamimidoyl)] from 5- and 6-bromo-3-fluoro-2-cyanopyridines and a wide range of easily available and bench-stable terminal alkynes, using Sonogashira cross-coupling, as the first step was disclosed. The generation of the polar amidoxime group was realized at a late stage upon treatment of the alkynylfluorocyanopyridine I [R = 4-EtC₆H₄, 3-pyridyl, tridecyl, etc.; R¹ = CN] by hydroxylamine. This mild and operationally simple two-step room temperature process was compatible with enantiopure chiral substrates and various functionality including free alcs., unprotected and CBz-protected amines, acetonides, benzyl ethers, amide, imide, di-substituted alkynes and strained saturated heterocycles.

European Journal of Organic Chemistry published new progress about 1256788-71-2. 1256788-71-2 belongs to nitriles-buliding-blocks, auxiliary class Pyridine,Fluoride,Nitrile,Bromide, name is 6-Bromo-3-fluoropicolinonitrile, and the molecular formula is C6H2BrFN2, Quality Control of 1256788-71-2.

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

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

Kita, Yusuke published the artcileRhodium-Catalyzed Alkenylation of Nitriles via Silicon-Assisted C-CN Bond Cleavage, Category: nitriles-buliding-blocks, the publication is Organic Letters (2010), 12(8), 1864-1867, database is CAplus and MEDLINE.

Rhodium-catalyzed Mizoroki-Heck type reaction of nitriles via the cleavage of C-C bonds is described. Orthogonal and iterative functionalizations of arenes were also demonstrated by combining the present and conventional halide-based cross-coupling reactions.

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, Category: nitriles-buliding-blocks.

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

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

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

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