Category: 238088-16-9

Qiao, Jin-Bao published the artcileAllylboronates from Vinyl Triflates and α-Chloroboronates by Reductive Nickel Catalysis, Recommanded Product: 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)butanenitrile, the publication is Organic Letters (2020), 22(13), 5085-5089, database is CAplus and MEDLINE.

Allylboronates are unique building blocks widely used in organic synthesis, but the construction of cyclic allylboranates remains a challenging subject. The authors demonstrate here a mild and efficient access to this type of compound through the cross-electrophile coupling of vinyl triflates and α-chloroboronates. The reaction proceeded with a good substrate scope and good functional group compatibility. The ready availability of vinyl triflates from ketones, as well as the rich chem. of allylboranates, makes the authors’ method suitable for the divergent modification of biol. active compounds Preliminary mechanistic studies revealed that α-chloroboronates were activated via a radical process.

Organic Letters 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 C10H18BNO2, Recommanded Product: 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)butanenitrile.

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

Pang, Maofu published the artcileAddition of a B-H Bond across an Amido-Cobalt Bond: Co^II-H-Catalyzed Hydroboration of Olefins, Product Details of C10H18BNO2, the publication is Organometallics (2018), 37(9), 1462-1467, database is CAplus.

This paper describes a well-defined cobalt(II) half-sandwich complex bearing a phosphinoaminato ligand, Cp*Co(1,2-Ph₂PC₆H₄NH) (1), that can activate pinacolborane (HBpin) for catalytic terminal hydroboration of olefins. The cooperative cobalt(II)-amido reactivity in 1 enables the B-H bond cleavage, affording the 17-electron cobalt(II) hydride Cp*Co(1,2-Ph₂PC₆H₄N^H(Bpin)), abbreviated H1(Bpin), in which the borenium ion is captured by the uncoordinated nitrogen atom of the phosphinoaminato ligand. Hydroboration of the C:C bond can be promoted by a heteroatom such as N or O at the β-position of terminal alkenes. The mechanism of such hydroboration was established by various stoichiometric reactions based on the cobalt(II) hydride. With cooperative Co^II-N reactivity for the B-H bond cleavage, our catalysis depends on the Co^II-H hydride generated by the system itself.

Organometallics 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 C10H18BNO2, Product Details of C10H18BNO2.

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

Wang, Hui published the artcileSelective Coupling of 1,2-Bis-Boronic Esters at the more Substituted Site through Visible-Light Activation of Electron Donor-Acceptor Complexes, COA of Formula: C10H18BNO2, the publication is Angewandte Chemie, International Edition (2022), 61(18), e202202061, database is CAplus and MEDLINE.

1,2-Bis-boronic esters are useful synthetic intermediates particularly as the two boronic esters can be selectively functionalized. Usually, the less hindered primary boronic ester reacts, but herein, we report a coupling reaction that enables the reversal of this selectivity. This is achieved through the formation of a boronate complex with an electron-rich aryllithium which, in the presence of an electron-deficient aryl nitrile, leads to the formation of an electron donor-acceptor complex. Following visible-light photoinduced electron transfer, a primary radical is generated which isomerizes to the more stable secondary radical before radical-radical coupling with the arene radical-anion, giving β-aryl primary boronic ester products. The reactions proceed under catalyst-free conditions. This method also allows stereodivergent coupling of cyclic cis-1,2-bis-boronic esters to provide trans-substituted products, complementing the selectivity observed in the Suzuki-Miyaura reaction.

Angewandte Chemie, International Edition 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 C14H31NO2, COA of Formula: C10H18BNO2.

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

Qiu, Jian published the artcileNi-Catalyzed Radical-Promoted Defluoroalkylborylation of Trifluoromethyl Alkenes To Access gem-Difluorohomoallylic Boronates, Synthetic Route of 238088-16-9, the publication is Organic Letters (2022), 24(12), 2446-2451, database is CAplus and MEDLINE.

Gem-Difluoroalkenyl boronates are attractive synthons for constructing diverse gem-difluoroalkenes and organoboron compounds However, the strategies for the construction of gem-difluorohomoallyl boronates has scarcely been described. Herein, authors develop an efficient protocol for the construction of gem-difluorohomoallylic boronates through a Ni-catalyzed radical-promoted defluoroalkylborylation of α-trifluoromethyl alkenes with α-haloboronates under mild conditions. This reaction features a broad substrate scope with good functional group tolerance and diverse transformations.

Organic Letters 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 C10H18BNO2, Synthetic Route of 238088-16-9.

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

Plaza, Manuel published the artcileHeterocyclization and Spirocyclization Processes Based on Domino Reactions of N-Tosylhydrazones and Boronic Acids Involving Intramolecular Allylborylations of Nitriles, Quality Control of 238088-16-9, the publication is Chemistry – A European Journal (2018), 24(55), 14836-14843, database is CAplus and MEDLINE.

Polycyclic mols. featuring all-carbon quaternary bridgehead centers were synthesized through domino cyclizations between N-tosylhydrazones and boronic acids. Variations of the general cascade have been applied for the preparation of 3-quinuclidinones and related alkaloid-like scaffolds through transannular heterocyclizations. Moreover, the employment of 3-cyanopropyl and 4-cyanobutylboronic acids and α,β-unsaturated N-tosylhydrazones led to spirocycles through unprecedented formal [n+1] cyclizations, including the stereoselective spirocyclization of the Hajos-Parrish ketone. The common feature of all the new reactions described is the creation of an all-carbon quaternary center by formation of two Csp³-C bonds on the hydrazonic carbon atom. DFT-based calculations suggested the occurrence of cascade processes, which involve a diazo compound carboborylation followed by a 1,3-borotropic rearrangement on an intermediate allylboronic acid and a novel bora-aza-ene cyclization.

Chemistry – A European Journal 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 C10H18BNO2, Quality Control of 238088-16-9.

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

Suzuki, Kensuke published the artcile(o-Phenylenediamino)borylstannanes: Efficient Reagents for Borylation of Various Alkyl Radical Precursors, SDS of cas: 238088-16-9, the publication is Chemistry – A European Journal (2021), 27(12), 3968-3973, database is CAplus and MEDLINE.

(o-Phenylenediamino)borylstannanes were newly synthesized to achieve radical boryl substitutions of a variety of alkyl radical precursors. Dehalogenative, deaminative, dechalcogenative, and decarboxylative borylations proceeded in the presence of a radical initiator to give the corresponding organic B compounds Radical clock experiments and computational studies provided insights into the mechanism of the homolytic substitution (S_H2) of the borylstannanes with alkyl radical intermediates. DFT calculation disclosed that the phenylenediamino structure lowered the LUMO level including the vacant p-orbital on the B atom to enhance the reactivity to alkyl radicals in S_H2. Also, C(sp³)-H borylation of THF was accomplished using the triplet state of xanthone.

Chemistry – A European Journal 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 C14H23N, SDS of cas: 238088-16-9.

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

Sang, Ruocheng published the artcileChiral Benzothiophene Synthesis via Enantiospecific Coupling of Benzothiophene S-Oxides with Boronic Esters, Quality Control of 238088-16-9, the publication is Angewandte Chemie, International Edition (2021), 60(48), 25313-25317, database is CAplus and MEDLINE.

Benzothiophenes are valuable heterocycles that are widely used in medicines, agrochems., and materials science. Herein, a general method for the synthesis of enantioenriched 2,3-disubstituted benzothiophenes via a transition-metal-free C2-alkylation of benzothiophenes with boronic esters is reported. The reactions utilize benzothiophene S-oxides in lithiation-borylations to generate intermediate arylboronate complexes, and subsequent Tf₂O-promoted S-O bond cleavage to trigger a Pummerer-type 1,2-metalate shift, which gives the coupled products with complete enantiospecificity. Primary, secondary and tertiary alkyl boronic esters and aryl boronic esters are successfully coupled with a range of C3-substituted benzothiophenes. Importantly, this transformation does not require the use of C3 directing groups, therefore it overcomes a major limitation of previously developed transition-metal-mediated C2 alkylations of benzothiophenes.

Angewandte Chemie, International Edition 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 C10H18BNO2, Quality Control of 238088-16-9.

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

Shu, Chao published the artcileMetal-free photoinduced C(sp³)-H borylation of alkanes, Recommanded Product: 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)butanenitrile, the publication is Nature (London, United Kingdom) (2020), 586(7831), 714-719, database is CAplus and MEDLINE.

Boronic acids and their derivatives are some of the most useful reagents in the chem. sciences, with applications spanning pharmaceuticals, agrochems. and functional materials. Catalytic C-H borylation is a powerful method for introducing these and other boron groups into organic mols. because it can be used to directly functionalize C-H bonds of feedstock chems. without the need for substrate pre-activation. These reactions have traditionally relied on precious-metal catalysts for C-H bond cleavage and, as a result, display high selectivity for borylation of aromatic C(sp²)-H bonds over aliphatic C(sp³)-H bonds. Here we report a mechanistically distinct, metal-free borylation using hydrogen atom transfer catalysis, in which homolytic cleavage of C(sp³)-H bonds produces alkyl radicals that are borylated by direct reaction with a diboron reagent. The reaction proceeds by violet-light photoinduced electron transfer between an N-alkoxyphthalimide-based oxidant and a chloride hydrogen atom transfer catalyst. Unusually, stronger Me C-H bonds are borylated preferentially over weaker secondary, tertiary and even benzylic C-H bonds. Mechanistic studies indicate that the high Me selectivity is a result of the formation of a chlorine radical-boron ‘ate’ complex that selectively cleaves sterically unhindered C-H bonds. By using a photoinduced hydrogen atom transfer strategy, this metal-free C(sp³)-H borylation enables unreactive alkanes to be transformed into valuable organoboron reagents under mild conditions and with selectivities that contrast with those of established metal-catalyzed protocols.

Nature (London, United Kingdom) 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 C3H9ClOS, Recommanded Product: 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)butanenitrile.

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

Shu, Chao published the artcilePhotoredox-Catalyzed Cyclobutane Synthesis by a Deboronative Radical Addition-Polar Cyclization Cascade, SDS of cas: 238088-16-9, the publication is Angewandte Chemie, International Edition (2019), 58(12), 3870-3874, database is CAplus and MEDLINE.

Photoredox-catalyzed methylcyclobutanations of boronic esters are described. The reactions proceed through single-electron transfer induced deboronative radical addition to an electron-deficient alkene followed by single-electron reduction and polar 4-exo-tet cyclization with a pendant alkyl halide. Key to the success of the methodol. was the use of easily oxidizable arylboronate complexes. Structurally diverse cyclobutanes are shown to be conveniently prepared from readily available boronic esters and a range of haloalkyl alkenes. The mild reactions display excellent functional group tolerance, and the radical addition-polar cyclization cascade also enables the synthesis of 3-, 5-, 6-, and 7-membered rings.

Angewandte Chemie, International Edition 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 C11H10O3, SDS of cas: 238088-16-9.

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

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