Tag: M.W=150-200

Speckmeier, Elisabeth published the artcileART – An Amino Radical Transfer Strategy for C(sp²)-C(sp³) Coupling Reactions, Enabled by Dual Photo/Nickel Catalysis, COA of Formula: C10H18BNO2, the publication is Journal of the American Chemical Society (2022), 144(22), 9997-10005, database is CAplus and MEDLINE.

Introducing the novel concept of amino radical transfer (ART) enabled the use of easily accessible and com. available alkyl boronic esters as cross coupling partners for aryl halides in dual photoredox/nickel catalysis mediated by visible light. Activation of otherwise photochem. innocent boronic esters by radicals generated from primary or secondary alkylamines gaves rise to an outstanding functional group tolerance in a mild, fast and air stable reaction. As shown in more than 50 examples including unprotected alcs., amines and carboxylic acids, ArR [Ar = 4-MeOC₆H₄, 4-MeC(O)HNC₆H₄, 3-pyridyl, etc.; R = cyclohexyl, 1-tert-butoxycarbonyl-4-piperidyl, Bn, etc.] this reaction allowed to quickly build up relevant scaffolds for organic synthesis and medicinal chem. In comparison with existing methods for C(sp²)-C(sp³) couplings an extraordinary generality could be realized via the ART concept, employing a single set of optimized reaction conditions. Due to its selectivity, the transformation could also be used for late-stage functionalization, as demonstrated with three exemplary syntheses of drug mols. Furthermore, the successful one-to-one scalability of this reaction up to gram scale without the necessity of any further precautions or flow systems was demonstrated.

Journal of the American Chemical Society published new progress about 238088-16-9. 238088-16-9 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Boronic acid and ester,Aliphatic cyclic hydrocarbon,Boronic Acids,Boronate Esters, name is 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)butanenitrile, and the molecular formula is C12H16O3, COA of Formula: C10H18BNO2.

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

Naveen, Togati published the artcileA Predictably Selective Nitration of Olefin with Fe(NO₃)₃ and TEMPO, Category: nitriles-buliding-blocks, the publication is Journal of Organic Chemistry (2013), 78(12), 5949-5954, database is CAplus and MEDLINE.

Ferric nitrate with catalytic TEMPO has been identified as a useful reagent for regio- and stereoselective nitration of a wide variety of aromatic, aliphatic, and heteroaromatic olefins. This reaction provided nitroolefins in preparatively useful yields with excellent E-selectivity. Due to its mild nature and operational simplicity, the present protocol is expected to find application in synthetic setup.

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 C9H6N2O2, Category: nitriles-buliding-blocks.

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

Sharma, Pragati R. published the artcileExperimental and computational studies on the Cinchona anchored calixarene catalysed asymmetric Michael addition reaction, HPLC of Formula: 5153-73-1, the publication is Chemical Communications (Cambridge, United Kingdom) (2022), 58(52), 7249-7252, database is CAplus and MEDLINE.

Lower-rim Cinchona anchored calix[4]arene cationic catalysts were developed for asym. Michael addition of acetylacetone to β-nitrostyrenes. The desired Michael adducts were formed with high yields and enantioselectivities. D. functional theory investigations throw light on the catalyst-substrate interaction and the reaction mechanism.

Chemical Communications (Cambridge, United Kingdom) 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 C19H14Cl2, HPLC of Formula: 5153-73-1.

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

Maity, Soham published the artcileEfficient and Stereoselective Nitration of Mono- and Disubstituted Olefins with AgNO₂ and TEMPO, Quality Control of 5153-73-1, the publication is Journal of the American Chemical Society (2013), 135(9), 3355-3358, database is CAplus and MEDLINE.

Nitroolefins are common and versatile reagents. Their synthesis from olefins is generally limited by the formation of mixtures of cis and trans compounds Here the authors report that silver nitrite (AgNO₂) along with TEMPO can promote the regio- and stereoselective nitration of a broad range of olefins. This work discloses a new and efficient approach wherein, starting from olefin, nitroalkane radical formation and subsequent transformations lead to the desired nitroolefin in a stereoselective manner.

Journal of the American Chemical Society 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

Wu, Ao-rong published the artcileSynthesis of aromatic acyl cyanides catalyzed by Sm(OTf)₃, COA of Formula: C8H6ClN, the publication is Nongyao (2013), 52(4), 241-243, 246, database is CAplus.

The paper aimed to study a new synthetic method of aromatic acyl cyanides. Catalyzed by samarium triflate [Sm(OTf)₃] aromatic acyl chlorides was reacted with sodium cyanide to give aromatic acyl cyanides. Under the optimal reaction conditions, the yields and purities of aromatic acyl products reached about 90% and above 98% resp. It was a novel practical method to prepare aromatic acyl cyanides, with mild reaction conditions and high selectivity, and without the use of phase transfer catalyst.

Nongyao 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 C23H23ClN2O4, COA of Formula: C8H6ClN.

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

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

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, 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

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