Tag: M.W=200-250

Tobisu, Mamoru published the artcileRhodium(I)-Catalyzed Borylation of Nitriles through the Cleavage of Carbon-Cyano Bonds, SDS of cas: 214360-44-8, the publication is Journal of the American Chemical Society (2012), 134(1), 115-118, database is CAplus and MEDLINE.

The reaction of aryl cyanides with diboron in the presence of a [RhCl(cod)]₂/Xantphos catalyst and 1 equivalent DABCO affords arylboronic esters via C-cyano bond cleavage. E.g., reaction of PhCN with 2 equivalent of bis(neopentanediolato)diboron in the presence of 5 mol% [RhCl(cod)]₂/10 mol% Xantphos and 1 equivalent of DABCO in toluene at 100° to give 73% yield of 5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane. This unprecedented mode of reactivity for a borylrhodium species allows the regioselective introduction of a boryl group in a late stage of synthesis.

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 C6H9N3O2, SDS of cas: 214360-44-8.

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

Kinuta, Hirotaka published the artcileNovel synthetic approach to arylboronates via rhodium-catalyzed carbon-cyano bond cleavage of nitriles, Category: nitriles-buliding-blocks, the publication is Synthesis (2012), 44(19), 2999-3002, database is CAplus.

A new rhodium-catalyzed method for preparing arylboronates from aryl cyanides through the cleavage of carbon-cyano bonds is described. This unprecedented transformation of nitriles allows the use of a cyano group as a boryl equivalent and the regioselective introduction of a boryl group at a late stage of the synthesis.

Synthesis 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

Tobisu, Mamoru published the artcileRhodium-catalyzed silylation and intramolecular arylation of nitriles via the silicon-assisted cleavage of carbon-cyano bonds, Name: 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, the publication is Journal of the American Chemical Society (2008), 130(47), 15982-15989, database is CAplus and MEDLINE.

Aryl and heterocyclic nitriles undergo substitution of the cyano-group by a silyl moiety in rhodium-catalyzed silylation by disilanes, yielding the corresponding aryl- and heterocyclic silanes. Reaction of RC₆H₄CN with Me₃SiSiMe₃ catalyzed by [Rh(cod)Cl]₂ or [Rh(OMe)(cod)]₂ gave the corresponding silylarenes, RC₆H₄SiMe₃ (R = 4-CF₃, 4-F, 4-CO₂Et, 4-CO₂^tBu, 4-CONH^tBu, 4-CONMe^tBu, 4-OAc, 4-OMe, 4-NMe₂, 3-OMe, 3-CO₂Et, 2-Me, 2-CF₃, 4-boronato). 2- And 1-Naphthalenecarbonitriles gave 2- and 1-naphthyltrimethylsilanes, resp. 1-Tosyl-2-pyrrolecarbonitrile, 1-tosyl-3-indolecarbonitrile, 3-quinolinecarbonitrile and ferrocenecarbonitrile were converted into the corresponding silanes with 57-81% yields. Under these catalytic conditions, carbon-cyano bonds in aryl, alkenyl, allyl, and benzyl cyanides bearing a variety of functional groups can be silylated. The observation of an enamine side product in the silylation of benzyl cyanides and related stoichiometric studies indicate that the carbon-cyano bond cleavage proceeds through the deinsertion of silyl isocyanide from η²-iminoacyl complex. A new intramol. biaryl coupling reaction of 2-NCC₆H₄OC₆H₄X-2 (X = Br, Cl), giving dibenzofuran, in which aryl cyanides and aryl chlorides are cross-coupled, is developed.

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 C3H5BN2O2, Name: 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile.

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

Tobisu, Mamoru published the artcileRh(I)-Catalyzed Silylation of Aryl and Alkenyl Cyanides Involving the Cleavage of C-C and Si-Si Bonds, HPLC of Formula: 214360-44-8, the publication is Journal of the American Chemical Society (2006), 128(25), 8152-8153, database is CAplus and MEDLINE.

The Rh(I)-catalyzed silylation of nitriles with disilanes is described. The cleavage of inert carbon-cyano and silicon-silicon bonds occurs in this catalysis. Thus, [RhCl(COD)]₂-catalyzed silylation of 2-cyanonaphthalene with Me₃SiSiMe₃ in ethylcyclohexane at 130° for 15h gave 87% 2-trimethylsilylnaphthalene.

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 C22H18Cl2N2, HPLC of Formula: 214360-44-8.

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

Jagadeesh, Rajenahally V. published the artcile‘Nanorust’-catalyzed Benign Oxidation of Amines for Selective Synthesis of Nitriles, Related Products of nitriles-buliding-blocks, the publication is ChemSusChem (2015), 8(1), 92-96, database is CAplus and MEDLINE.

The selective and environmentally benign oxidative conversion of primary amines for the synthesis of structurally diverse aromatic, aliphatic and heterocyclic nitriles using a reusable ‘nanorust’ (nanoscale Fe₂O₃)-based catalysts applying mol. oxygen is reported.

ChemSusChem published new progress about 261951-87-5. 261951-87-5 belongs to nitriles-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Nitrile,Benzene,Ether, name is 4-Methoxy-3-(trifluoromethyl)benzonitrile, and the molecular formula is C9H6F3NO, Related Products of nitriles-buliding-blocks.

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

Delaney, Connor P. published the artcilePotassium Trimethylsilanolate Enables Rapid, Homogeneous Suzuki-Miyaura Cross-Coupling of Boronic Esters, Related Products of nitriles-buliding-blocks, the publication is ACS Catalysis (2020), 10(1), 73-80, database is CAplus and MEDLINE.

Herein, a mild and operationally simple method for the Suzuki-Miyaura cross-coupling of boronic esters is described. Central to this advance is the use of the organic-soluble base, potassium trimethylsilanolate, which allows for a homogeneous, anhydrous cross-coupling. The coupling proceeds at a rapid rate, often furnishing products in quant. yield in less than 5 min. By applying this method, a >10-fold decrease in reaction time was observed for three published reactions which required >48 h to reach satisfactory conversion.

ACS Catalysis 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, Related Products of nitriles-buliding-blocks.

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

Natte, Kishore published the artcilePalladium-Catalyzed Trifluoromethylation of (Hetero)Arenes with CF₃Br, Formula: C9H6F3NO, the publication is Angewandte Chemie, International Edition (2016), 55(8), 2782-2786, database is CAplus and MEDLINE.

The CF₃ group is an omnipresent motif found in many pharmaceuticals, agrochems., catalysts, materials, and industrial chems. Despite well-established trifluoromethylation methodologies, the straightforward and selective introduction of such groups into (hetero)arenes using available and less expensive sources is still a major challenge. In this regard, the selective synthesis of various trifluoromethyl-substituted (hetero)arenes by palladium-catalyzed C-H functionalization is herein reported. This novel methodol. proceeds under comparably mild reaction conditions with good regio- and chemoselectivity. As examples, trifluoromethylations of biol. important mols., such as melatonin, theophylline, caffeine, and pentoxifylline, are showcased.

Angewandte Chemie, International Edition published new progress about 261951-87-5. 261951-87-5 belongs to nitriles-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Nitrile,Benzene,Ether, name is 4-Methoxy-3-(trifluoromethyl)benzonitrile, and the molecular formula is C9H6F3NO, Formula: C9H6F3NO.

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

Mills, L. Reginald published the artcileCobalt-Catalyzed C(sp²)-C(sp³) Suzuki-Miyaura Cross-Coupling Enabled by Well-Defined Precatalysts with L,X-Type Ligands, Quality Control of 214360-44-8, the publication is ACS Catalysis (2022), 12(3), 1905-1918, database is CAplus and MEDLINE.

Cobalt(II) halides in combination with phenoxyimine (FI) ligands generated efficient precatalysts in situ for the C(sp²)-C(sp³) Suzuki-Miyaura cross-coupling between alkyl bromides and neopentylglycol (hetero)arylboronic esters. The protocol enabled efficient C-C bond formation with a host of nucleophiles and electrophiles (36 examples, 34-95%) with precatalyst loadings of 5 mol %. Studies with alkyl halide electrophiles that function as radical clocks support the intermediacy of alkyl radicals during the course of the catalytic reaction. The improved performance of the FI-cobalt catalyst was correlated with decreased lifetimes of cage-escaped radicals as compared to those of diamine-type ligands. Studies of the phenoxy(imine)-cobalt coordination chem. validate the L,X interaction leading to the discovery of an optimal, well-defined, air-stable mono-FI-cobalt(II) precatalyst structure.

ACS Catalysis 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

Kang, Taeho published the artcileAlkene Difunctionalization Directed by Free Amines: Diamine Synthesis via Nickel-Catalyzed 1,2-Carboamination, SDS of cas: 214360-44-8, the publication is ACS Catalysis (2022), 12(7), 3890-3896, database is CAplus.

A versatile method to access differentially substituted 1,3- and 1,4-diamines RNH(CH₂)₂CH(R¹)CH₂R² (R = H, Me, Bn, pyrimidin-2-yl, etc.; R¹ = piperidin-1-yl, 1,4-dioxa-8-azaspiro[4.5]decan-8-yl, diethylaminyl; R² = Ph, naphthalen-1-yl, 1-benzofuran-5-yl, etc.) via a nickel-catalyzed three-component 1,2-carboamination of alkenyl amines RNH(CH₂)₂CH=CH₂ with aryl/alkenylboronic ester nucleophiles R³COOR¹ (R³ = t-Bu, Ph, morpholin-4-yl, etc.) and N-O electrophiles R²B(nep) was reported. The reaction proceeds efficiently with free primary and secondary amines without needing a directing auxiliary or protecting group, and is enabled by fine-tuning the leaving group on the N-O reagent. The transformation is highly regioselective and compatible with a wide range of coupling partners and alkenyl amine substrates, all performed at room temperature A series of kinetic studies support a mechanism in which alkene coordination to the nickel catalyst is turnover-limiting.

ACS Catalysis 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

Shen, Yan published the artcileCopper-catalyzed direct C-H arylation of pyridine N-oxides with arylboronic esters: one-pot synthesis of 2-arylpyridines, HPLC of Formula: 214360-44-8, the publication is Chemical Communications (Cambridge, United Kingdom) (2014), 50(33), 4292-4295, database is CAplus and MEDLINE.

The first example of the copper-catalyzed direct C-H arylation of pyridine N-oxides with arylboronic esters has been developed, leading to a wide range of 2-arylpyridines in a one-pot synthesis with moderate to good yields without an addnl. reductant. This transformation allows for rapid access to a variety of 2-arylpyridines using an inexpensive catalytic system that would be more difficult to access with traditional methods. Thus, this method represents a simple and practical procedure to access 2-arylpyridines.

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 C44H28ClFeN4, HPLC of Formula: 214360-44-8.

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