Category: 608534-44-7

Zhang, Yahui published the artcileSelective electrocatalytic hydroboration of aryl alkenes, Application In Synthesis of 608534-44-7, the publication is Green Chemistry (2021), 23(4), 1691-1699, database is CAplus.

Organoboron compounds are powerful precursors of value-added organic compounds in synthetic chem., and transition metal-catalyzed borylation has always been dominant. To avoid toxic reagents and costs associated with metal catalysts, simpler, more economical and effective approaches for delivering organoborons are highly desirable. Here, without the use of any metal catalysts, a CH₃CN-involved electrochem. borylation reaction is reported with alkenes and HBpin as substrates. The site-selectivity is realized to achieve mono- or di-functional borylation of an unsaturated bond by regulating the proportion of HBpin. In addition, the success of gram-scale experiments and versatile conversions confirms the potential applications of this strategy in industrial synthesis. The vital auxiliary role of N,N-diisopropylethylamine (DIEA) in the process of acetonitrile electrolysis is disclosed in the mechanism study. The proposed new strategy provides a generic platform for the discovery of addnl. challenging electrochem. systems for hydrogenation reactions.

Green Chemistry published new progress about 608534-44-7. 608534-44-7 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic,Boronic acid and ester,Boronate Esters,Boronic Acids,Boronic acid and ester, name is 2-(2,3-Dihydro-1H-inden-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, and the molecular formula is C12H14O, Application In Synthesis of 608534-44-7.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Zhao, Qiuting published the artcileGroup 4 Metallocene Complexes Supported by a Redox-Active O,C-Chelating Ligand, Recommanded Product: 2-(2,3-Dihydro-1H-inden-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, the publication is Organometallics (2022), 41(12), 1488-1500, database is CAplus.

Group 4 metallocene complexes Cp₂M[OC] (Cp = η⁵-C₅H₅; M = Ti (1) or Zr (2); [OC] = κ²-O,C-OC₆H₂-2-CPh₂-4,6-^tBu₂) supported with a redox-active bidentate O,C-ligand were successfully synthesized through salt metathesis. X-ray crystallog. results showed that both complexes maintained similar bent metallocene coordination geometry. A close inspection of the structural parameters revealed a remarkably long Ti-C bond in 1, indicating concomitant intramol. charge transfer upon metathesis and coordination. The electronic structure of 1 was studied by EPR measurements, revealing the presence of a Ti(III) center and one [OC]^•- radical anion. In contrast, the diamagnetic complex 2 was found to comprise a Zr(IV) center and an alkyl/aryloxo dianion. Divergent catalytic reactivity was observed for the two Group 4 derivatives in the reaction between alkenes and HBpin. Specifically, dehydrogenative boration products (i.e., vinyl boronate esters) were obtained exclusively in the presence of the Zr complex (18 examples, up to 90% yield), while the Ti compound selectively promoted the formation of alkyl boronate esters via hydroboration (19 examples, up to 99% yield).

Organometallics published new progress about 608534-44-7. 608534-44-7 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic,Boronic acid and ester,Boronate Esters,Boronic Acids,Boronic acid and ester, name is 2-(2,3-Dihydro-1H-inden-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, and the molecular formula is C48H47FeP, Recommanded Product: 2-(2,3-Dihydro-1H-inden-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Fasano, Valerio published the artcileDivergent, Stereospecific Mono- and Difluoromethylation of Boronic Esters, Computed Properties of 608534-44-7, the publication is Angewandte Chemie, International Edition (2020), 59(22), 8502-8506, database is CAplus and MEDLINE.

There is considerable interest in incorporating fluorine into agrochems. and pharmaceuticals to improve their biol. properties. While a number of methods have been reported for installing CH₂F and CHF₂ groups, they are mainly limited to radical reactions, which are invariably racemic. Herein, we report the divergent, stereospecific reaction of fluoroiodomethyllithium with boronic esters to give α-fluoro-boronic esters. These unique intermediates can be readily transformed into the corresponding mono- or difluoromethylated compounds through proto- or fluorodeboronation, resp. The use of the highly unstable fluoroiodomethyllithium was key to allowing rapid 1,2-migration over competing decomposition of the carbanion. DFT calculations informed and supported the exptl. findings. Thus, e.g., homologation of I with FCH₂I/LDA → II (90%); protodeboronation using 4-tBu-catechol/TFA afforded III (90%).

Angewandte Chemie, International Edition published new progress about 608534-44-7. 608534-44-7 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic,Boronic acid and ester,Boronate Esters,Boronic Acids,Boronic acid and ester, name is 2-(2,3-Dihydro-1H-inden-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, and the molecular formula is C15H21BO2, Computed Properties of 608534-44-7.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Kleinmans, Roman published the artcilePhotoredox-enabled 1,2-dialkylation of α-substituted acrylates via Ireland-Claisen rearrangement, Safety of 2-(2,3-Dihydro-1H-inden-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, the publication is Chemical Science (2021), 12(8), 2816-2822, database is CAplus and MEDLINE.

The 1,2-dialkylation of simple feedstock acrylates RC(=CH₂)C(O)OR¹ [R = H, Me, F, i-Pr, naphthalen-1-yl, etc.; R¹ = prop-2-en-1-yl, 4-ethenyloxan-4-yl, 2-chloroprop-2-en-1-yl, 2-(4-oxocyclohexylidene)ethyl, etc.] for the synthesis of valuable tertiary carboxylic acids R²CH₂C(R)(R³)C(O)OH [R² = cyclohexyl, oxan-4-yl, 5-(2,5-dimethylphenoxy)-2-methylpentan-2-yl, etc.; R³ = prop-2-en-1-yl, 2-(oxan-4-ylidene)ethyl, 2-chloroprop-2-en-1-yl, etc.] by merging Giese-type radical addition with an Ireland-Claisen rearrangement have been reported. Key to success is the utilization of the reductive radical-polar crossover concept under photocatalytic reaction conditions to force the [3,3]-sigmatropic rearrangement after alkyl radical addition to allyl acrylates. Using readily available alkyl boronic acids as radical progenitors, this redox-neutral, transition-metal-free protocol allows the mild formation of two C(sp³)-C(sp³) bonds, thus providing rapid access to complex tertiary carboxylic acids in a single step. Moreover, this strategy enables the efficient synthesis of highly attractive α,α-dialkylated γ-amino butyric acids (GABAs) R⁴(CH₂)₂C(CH₃)(CH₂CH=CH₂)C(O)OH [R⁴ = dibutylaminyl, morpholin-4-yl, 4-[2-(morpholin-4-yl)-2-oxoethyl]piperazin-1-yl, etc.] when α-silyl amines R⁴CH₂Si(CH₃)₃ are used as radical precursors – a structural motif that was still inaccessible in related transformations. Depending on the nature of the radical precursors and their inherent oxidation potentials, either a photoredox-induced radical chain or a solely photoredox mechanism is proposed to be operative.

Chemical Science published new progress about 608534-44-7. 608534-44-7 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic,Boronic acid and ester,Boronate Esters,Boronic Acids,Boronic acid and ester, name is 2-(2,3-Dihydro-1H-inden-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, and the molecular formula is C15H21BO2, Safety of 2-(2,3-Dihydro-1H-inden-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Hu, Jiefeng published the artcileSelective C-N Borylation of Alkyl Amines Promoted by Lewis Base, Application of 2-(2,3-Dihydro-1H-inden-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, the publication is Angewandte Chemie, International Edition (2018), 57(46), 15227-15231, database is CAplus and MEDLINE.

An efficient method for the metal-free deaminative borylation of alkylamines, using bis(catecholato)diboron as the B source, to directly synthesize various alkyl K trifluoroborate salts is introduced. The key to this high reactivity is the use of pyridinium salt activated alkylamines, with a catalytic amount of a bipyridine-type Lewis base as a promoter. This transformation shows good functional-group compatibility (e.g., it is unimpeded by the presence of a ketone, indole, internal alkene, or unactivated alkyl chloride) and can serve as a powerful synthetic tool for borylation of amine groups in complex compounds Mechanistic experiments and computations suggest a mechanism in which the Lewis base activated B₂cat₂ unit intercepts an alkyl radical generated by single-electron transfer (SET) from a B-based reductant.

Angewandte Chemie, International Edition published new progress about 608534-44-7. 608534-44-7 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic,Boronic acid and ester,Boronate Esters,Boronic Acids,Boronic acid and ester, name is 2-(2,3-Dihydro-1H-inden-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, and the molecular formula is C15H21BO2, Application of 2-(2,3-Dihydro-1H-inden-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Fawcett, Alexander published the artcileStrain-Release-Driven Homologation of Boronic Esters: Application to the Modular Synthesis of Azetidines, Computed Properties of 608534-44-7, the publication is Journal of the American Chemical Society (2019), 141(11), 4573-4578, database is CAplus and MEDLINE.

Azetidines are important motifs in medicinal chem., but there are a limited number of methods for their synthesis. Herein, the authors present a new method for their modular construction by exploiting the high ring strain associated with azabicyclo[1.1.0]butane. Generation of azabicyclo[1.1.0]butyl lithium followed by its trapping with a boronic ester gives an intermediate boronate complex which, upon N-protonation with acetic acid, undergoes 1,2-migration with cleavage of the central C-N bond to relieve ring strain. The methodol. is applicable to primary, secondary, tertiary, aryl, and alkenyl boronic esters and occurs with complete stereospecificity. The homologated azetidinyl boronic esters can be further functionalized through reaction of the N-H azetidine, and through transformation of the boronic ester. The methodol. was applied to a short, stereoselective synthesis of the azetidine-containing pharmaceutical, cobimetinib.

Journal of the American Chemical Society published new progress about 608534-44-7. 608534-44-7 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic,Boronic acid and ester,Boronate Esters,Boronic Acids,Boronic acid and ester, name is 2-(2,3-Dihydro-1H-inden-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, and the molecular formula is C15H21BO2, Computed Properties of 608534-44-7.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – 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, Application of 2-(2,3-Dihydro-1H-inden-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 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 608534-44-7. 608534-44-7 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic,Boronic acid and ester,Boronate Esters,Boronic Acids,Boronic acid and ester, name is 2-(2,3-Dihydro-1H-inden-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, and the molecular formula is C18H10F3NO3S2, Application of 2-(2,3-Dihydro-1H-inden-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Zhang, Wen published the artcileElectrochemically driven cross-electrophile coupling of alkyl halides, Product Details of C15H21BO2, the publication is Nature (London, United Kingdom) (2022), 604(7905), 292-297, database is CAplus and MEDLINE.

Here, electrochem. were used to achieve the differential activation of alkyl halides e.g., 2-(2-bromopropan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (I) by exploiting their disparate electronic and steric properties. Specifically, the selective cathodic reduction of a more substituted alkyl halide (I) gives rise to a carbanion, which undergoes preferential coupling with a less substituted alkyl halide via bimol. nucleophilic substitution to forge a new carbon-carbon bond. This protocol enables efficient cross-electrophile coupling of a variety of functionalized and unactivated alkyl electrophiles in the absence of a transition metal catalyst, and shows improved chemoselectivity compared with existing methods.

Nature (London, United Kingdom) published new progress about 608534-44-7. 608534-44-7 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic,Boronic acid and ester,Boronate Esters,Boronic Acids,Boronic acid and ester, name is 2-(2,3-Dihydro-1H-inden-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, and the molecular formula is C10H10O2, Product Details of C15H21BO2.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Shao, Xinxin published the artcileCopper-Catalyzed Trifluoromethylthiolation of Primary and Secondary Alkylboronic Acids, COA of Formula: C15H21BO2, the publication is Organic Letters (2014), 16(18), 4738-4741, database is CAplus and MEDLINE.

A Cu-catalyzed trifluoromethylthiolation of primary and secondary alkylboronic acids with an electrophilic trifluoromethylthiolating reagent is described. Tolerance for a variety of functional groups was observed

Organic Letters published new progress about 608534-44-7. 608534-44-7 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic,Boronic acid and ester,Boronate Esters,Boronic Acids,Boronic acid and ester, name is 2-(2,3-Dihydro-1H-inden-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, and the molecular formula is C12H9NO, COA of Formula: C15H21BO2.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Wei, Dian published the artcileDecarboxylative Borylation of mCPBA-Activated Aliphatic Acids, Formula: C15H21BO2, the publication is Organic Letters (2020), 22(1), 234-238, database is CAplus and MEDLINE.

A decarboxylative borylation of aliphatic acids for the synthesis of a variety of alkylboronates was developed by mixing m-chloroperoxybenzoic acid (mCPBA)-activated fatty acids with bis(catecholato)diboron in DMF at room temperature A radical chain process is involved in the reaction which initiates from the B-B bond homolysis followed by the radical transfer from the B atom to the C atom with subsequent decarboxylation and borylation.

Organic Letters published new progress about 608534-44-7. 608534-44-7 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic,Boronic acid and ester,Boronate Esters,Boronic Acids,Boronic acid and ester, name is 2-(2,3-Dihydro-1H-inden-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, and the molecular formula is C5H10O2S, Formula: C15H21BO2.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts