Nitriles-buliding-blocks

Liu, Yan-Kai published the artcileOpen-Close: An Alternative Strategy to α-Functionalization of Lactone via Enamine Catalysis in One Pot under Mild Conditions, Formula: C9H6N2O2, the publication is Organic Letters (2015), 17(8), 2022-2025, database is CAplus and MEDLINE.

An open-close strategy in asym. catalysis is newly developed. With this powerful strategy, lactols are directly applied as potential precursors of lactones in enamine-based asym. Michael reactions providing a facile access to α-functionalized lactones containing two adjacent stereogenic centers as a single diastereomer, e.g. I, in good to excellent yields (up to 99%) and with excellent enantioselectivities (most cases >99%). Moreover, the reaction products are shown to give highly functionalized derivatives by stepwise systematic transformations.

Organic Letters published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, Formula: C9H6N2O2.

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

Liu, Tang-Lin published the artcileCyano-borrowing: titanium-catalyzed direct amination of cyanohydrins with amines and enantioselective examples, Recommanded Product: 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, the publication is Chemical Communications (Cambridge, United Kingdom) (2020), 56(4), 651-654, database is CAplus and MEDLINE.

In the presence of Ti(Oi-Pr)₄, aldehyde and ketone cyanohydrins underwent amination reactions with amines such as 4-methoxyaniline to yield α-aminonitriles. Aryl, aryl alkyl, and dialkyl ketones and aryl and alkyl aldehyde cyanohydrins underwent amination. Reaction of aldehyde cyanohydrins with 4-methoxyaniline in the presence of Ti(Oi-Pr)₄, (S)-BINOL, and quinine yielded nonracemic (S)-α-aminonitriles in 31-88% ee. The reaction mechanism was studied; the reaction is proposed to occur by elimination of cyanide from the cyanohydrin followed by imine formation and addition of cyanide to the imine (“cyanide borrowing”) rather than by loss of a proton, imine formation, and reduction (“hydrogen borrowing”).

Chemical Communications (Cambridge, United Kingdom) published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C8H6ClNO, Recommanded Product: 2-(2-Chlorophenyl)-2-hydroxyacetonitrile.

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

Li, Qing-Hua published the artcileTitanium-Catalyzed Cyano-Borrowing Reaction for the Direct Amination of Cyanohydrins with Ammonia, Formula: C8H6ClNO, the publication is Organic Letters (2019), 21(20), 8429-8433, database is CAplus and MEDLINE.

Herein, the direct amination of cyanohydrins with the partner of ammonia for the synthesis of N-unprotected α-aminonitriles H₂NC(R¹)(R²)CN (R¹ = Ph, 4-FC₆H₄, 2-thienyl, etc.; R² = H, Me, Et; -R¹R²– = -(CH₂)₄-) is developed. The reaction proceeds via titanium-catalyzed cyano-borrowing reaction, which features high atom economy and simple operation. A broad range of ketone or aldehyde cyanohydrins was tolerated with ammonia, and the N-unprotected α-aminonitriles were synthesized with moderate to high yields under mild reaction conditions.

Organic Letters published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C8H6ClNO, Formula: C8H6ClNO.

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

Liu, Dong published the artcileNickel-Catalyzed Selective Oxidative Radical Cross-Coupling: An Effective Strategy for Inert Csp³-H Functionalization, COA of Formula: C12H14BNO2, the publication is Organic Letters (2015), 17(4), 998-1001, database is CAplus and MEDLINE.

An effective strategy for inert Csp³-H functionalization through nickel-catalyzed selective radical cross-couplings was demonstrated [e.g., PhB(OH)₂ + cyclohexane â†?phenylcyclohexane (73%) in presence of Ni(acac)₂, Ph₃P, dppb, K₃PO₄ as base, and di-tert-Bu peroxide as oxidant]. D. functional theory calculations were conducted and strongly supported the radical cross-coupling pathway assisted by nickel catalyst, which was further confirmed by radical-trapping experiments Different arylborates including arylboronic acids, arylboronic acid esters and 2,4,6-triarylboroxin were all good coupling partners, generating the corresponding Csp³-H arylation products in good yields.

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, COA of Formula: C12H14BNO2.

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

Huang, Ping published the artcileSilver(I)-catalyzed denitrative trifluoromethylation of β-nitrostyrenes with CF₃SO₂Na, Quality Control of 5153-73-1, the publication is Tetrahedron Letters (2016), 57(42), 4705-4708, database is CAplus.

A novel and convenient approach to the synthesis of substituted β-trifluoromethyl styrenes (E)-RCH=CHCF₃ (R = 2,4-Cl₂C₆H₃, 4-O₂NC₆H₄, naphthalen-2-yl, etc.) via a silver(I)-catalyzed denitrative trifluoromethylation of β-nitrostyrenes (E)-RCH=CHNO₂ with CF₃SO₂Na under relatively mild conditions has been developed. This protocol delivered excellent stereoselectivity and showed wide substrate tolerance.

Tetrahedron Letters published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, Quality Control of 5153-73-1.

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

Zhang, Yan published the artcileThe photochromic behaviour of two viologen salts modulated by the distances between the halide anions and the cationic N atoms of viologen, COA of Formula: C8H6ClN, the publication is Acta Crystallographica, Section C: Structural Chemistry (2019), 75(12), 1628-1634, database is CAplus and MEDLINE.

In recent years, viologens and their derivatives have received much attention due to their various potential applications, ranging from electro- or photochromic devices to clean energy. Generally, viologen compounds exhibit a color change upon being subjected to an external stimulus. However, the chromic mechanism is still ambiguous, because there are many electron-transfer pathways for a chromic compound that need to be considered. Thus, exploring new chromic viologen-based compounds with one pathway should be important and meaningful. In this article, two new viologen-based derivatives, namely 1-(2-cyanobenzyl)-4,4′-bipyridinium chloride (o-CBbpy·Cl), C₁₈H₁₄N₃⁺·Cl^– (1), and 1-(2-cyanobenzyl)-4,4′-bipyridinium bromide (o-CBbpy·Br), C₁₈H₁₄N₃⁺·Br^– (2), have been synthesized and characterized. Interestingly, both isomorphic compounds possess only one electron-transfer pathway, in which 1-(2-cyanobenzyl)-4,4′-bipyridinium cations (o-CBbpy) and halide anions are employed as electron donors and acceptors, resp. Salts 1 and 2 consist of o-CBbpy cations involved in p-p interactions and hydrogen-bond interactions, and halide anions weakly hydrogen bonded to the viologen cations. The salts show different photoresponsive characteristics under identical conditions, which should be mainly related to the distances between the halide cations and the cationic N atoms of o-CBbpy but not the electronegativities of the halogen atoms. These results should not only help in understanding that the distance of the electron-transfer pathway plays an important role in viologen-based photochromism, but should also guide the design and synthesis of addnl. photochromic materials.

Acta Crystallographica, Section C: Structural Chemistry published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C18H28B2O4, COA of Formula: C8H6ClN.

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

Zhou, Meng published the artcileA Metal-Free Three-Component Reaction of trans-β-Nitrostyrene Derivatives, Dibromo Amides, and Amines Leading to Functionalized Amidines, COA of Formula: C9H6N2O2, the publication is Journal of Organic Chemistry (2019), 84(2), 1015-1024, database is CAplus and MEDLINE.

Amidines such as I were prepared chemoselectively and diastereoselectively by three-component reactions of β-nitrostyrenes such as (E)-PhCH:CHNO₂ with BocNBr₂ or with N,N-dibromoamides generated in situ from amides and N-bromosuccinimide or N-chlorosuccinimide. A bisamidine and α,β-unsaturated amidines were prepared using this method. The mechanism of formation of I was studied by isolation of reaction intermediates and their further reaction; the α,α-dibromonitroalkane PhCH(NHBoc)CBr₂NO₂ [formed by addition of BocNBr₂ to (E)-PhCH:CHNO₂] underwent elimination to (Z)-PhC(NHBoc):CBrNO₂ which underwent C-C bond cleavage in the presence of base and morpholine to yield I.

Journal of Organic Chemistry published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C8H6ClNO, COA of Formula: C9H6N2O2.

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

Liu, Qiang published the artcilePalladium-Catalyzed Aerobic Oxidative Carbonylation of Arylboronate Esters under Mild Conditions, Recommanded Product: 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, the publication is Angewandte Chemie, International Edition (2010), 49(19), 3371-3374, S3371/1-S3371/38, database is CAplus and MEDLINE.

Oxidative carbonylation of arylboronic acid derivatives under balloon pressure of CO with air as the oxidant at 40-50 °C was used to prepare carboxylate esters. The optimized conditions for the oxidative carbonylation were 5 mol% of [PdCl₂(PPh₃)₂] as the catalyst, triethylamine as the base, and a ratio of air/CO 3:1 at 40 °C. E.g., reaction of 5,5-dimethyl-2-o-tolyl-1,3,2-dioxaborinane and BuOH under the optimized conditions gave 81% Bu 2-methylbenzoate.

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, Recommanded Product: 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile.

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

Wang, Hong-xue published the artcileStudy of scale up of fluorescent whitening agent ER-I, Recommanded Product: 2-(Chloromethyl)benzonitrile, the publication is Yingyong Huagong (2012), 41(9), 1658-1660, database is CAplus.

The fluorescent brightener ER-I was synthesized through Abuzov esterification and Witting condensation with the raw material tri-Et phosphite, 2-(chloromethyl) benzonitrile and 1, 4-phthalaldehyde. The influence factors such as reaction temperature, feeding method and the ratio of raw material were researched in detail. The optimum reaction condition was as follows: when the ratio of tri-Et phosphite : benzyl chloride 1.1:1.0 was used, temperature of feed was 140°C, the reaction time was 9 h, and the total yield 93%. The stabilization of technol. condition was confirmed by 6 time tests.

Yingyong Huagong published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C8H5IO, Recommanded Product: 2-(Chloromethyl)benzonitrile.

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

Wang, Xueqiang published the artcileMetal-Free Etherification of Aryl Methyl Ether Derivatives by C-OMe Bond Cleavage, HPLC of Formula: 261951-87-5, the publication is Organic Letters (2018), 20(14), 4267-4272, database is CAplus and MEDLINE.

Alkoxyaryl (particularly methoxyaryl) nitriles such as 2-methoxybenzonitrile underwent chemoselective etherification (nucleophilic aromatic substitution) reactions with alcs. mediated by KOt-Bu or KHMDS in 1,4-dioxane to yield different alkoxyaryl nitriles. Primary, secondary, and tertiary alcs. were effective, and natural product or pharmaceutical-derived alcs. were used; the method was used to prepare butoxycaine in three steps from 4-methoxybenzonitrile. 4-Cyanophenyl (+)-menthyl ether was converted to a variety of derivatives by nitrile functionalization reactions. DFT calculations and exptl. results are consistent with potassium ion-mediated activation of the methoxy group through binding to the nitrile and support an S_NAr mechanism for the etherification reaction.

Organic Letters 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 C18H12ClNO, HPLC of Formula: 261951-87-5.

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