Category: 78782-17-9

《Vinylidene Homologation of Boronic Esters and its Application to the Synthesis of the Proposed Structure of Machillene》 was written by Fordham, James M.; Grayson, Matthew N.; Aggarwal, Varinder K.. Product Details of 78782-17-9This research focused onvinylidene homologation boronic ester lithiated epoxysilane; machillene proposed structure synthesis; homologation; natural product; organoboron; stereospecificity; vinyl boronic ester. The article conveys some information:

Alkenyl boronic esters are important reagents in organic synthesis. Herein, we report that these valuable products can be accessed by the homologation of boronic esters with lithiated epoxysilanes [thus, e.g., treatment of epoxysilane I in pentane at -95° with TMEDA/tBuLi followed by addition of boronic ester II in pentane, stirring for 1 h, warming to -78° for an addnl. hour and finally warming to room temperature and then 40° for 1 h afforded III (77%)]. Aliphatic and electron-rich aromatic boronic esters provided vinylidene boronic esters in moderate to high yields, while electron-deficient aromatic and vinyl boronic esters were found to give the corresponding vinyl silane products. Through DFT calculations, this divergence in mechanistic pathway has been rationalized by considering the stabilization of neg. charge in the C-Si and C-B bond breaking transition states. This vinylidene homologation was used in a short six-step stereoselective synthesis of the proposed structure of machillene, however, synthetic and reported data were found to be inconsistent. In the experiment, the researchers used many compounds, for example, Bis[(pinacolato)boryl]methane(cas: 78782-17-9Product Details of 78782-17-9)

Bis[(pinacolato)boryl]methane(cas: 78782-17-9) belongs to organoboron compounds. Organoboron compounds are versatile intermediates and as such are some of the most important classes of reagents in modern organic chemistry. This stems from their ease of preparation combined with their ability to undergo a broad range of chemical transformations.Product Details of 78782-17-9

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In 2018,Iacono, Carmelo E.; Stephens, Thomas C.; Rajan, Teena S.; Pattison, Graham published 《A Coupling Approach for the Generation of α,α-Bis(enolate) Equivalents: Regioselective Synthesis of gem-Difunctionalized Ketones》.Journal of the American Chemical Society published the findings.Application of 78782-17-9 The information in the text is summarized as follows:

Regioselective α,α-difunctionalization adjacent to a ketone is a significant synthetic challenge. Here, we present a solution to this problem through the transition-metal-free coupling of esters with geminal bis(boron) compounds This forms an α,α-bis(enolate) equivalent which can be trapped with electrophiles including alkyl halides and fluorinating agents. This presents an efficient, convergent synthetic strategy for the synthesis of unsym. blocked ketones. After reading the article, we found that the author used Bis[(pinacolato)boryl]methane(cas: 78782-17-9Application of 78782-17-9)

Bis[(pinacolato)boryl]methane(cas: 78782-17-9) belongs to organoboron compounds. Organoboron compounds have been a cornerstone of synthetic transformations for decades. Areas such as boron-containing catalysts, metalate chemistry, photoredox methods, and boryl anions have brought significant new developments in understanding and provided new reactivity upon.Application of 78782-17-9

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In 2018,Armstrong, Roly J.; Nandakumar, Meganathan; Dias, Rafael M. P.; Noble, Adam; Myers, Eddie L.; Aggarwal, Varinder K. published 《Enantiodivergent Synthesis of Allenes by Point-to-Axial Chirality Transfer》.Angewandte Chemie, International Edition published the findings.Product Details of 78782-17-9 The information in the text is summarized as follows:

Nonracemic di-, tri-, and tetrasubstituted allenes were prepared by an enantiodivergent route using the homologation of (phenylselenyl)alkenylboronates such as I with lithiated alkyl diisopropylcarbamates generated with (+)-sparteine and s-BuLi and stereoselective oxidative syn-elimination and alkylative anti-elimination reactions as key steps. Nonracemic boronic esters such as II were prepared by homologation of α-seleno alkenyl boronic esters such as I with lithiated diisopropylcarbamates such as 4-MeOC6H4CH2CH2CH2OCONi-Pr2. Syn-elimination of II using mCPBA yielded the nonracemic (P)-allene III in >99% enantiospecificity, while anti-elimination of II by alkylation with MeOTf in CH2Cl2 followed by NaHCO3 in MeOH yielded (M)-allene IV in 98% enantiospecificity. By employing either oxidative or alkylative conditions, both syn and anti elimination could be achieved with complete stereospecificity. The process enables the synthesis of either M or P allenes from a single isomer of a point-chiral precursor and can be employed for the enantioselective assembly of di-, tri-, and tetrasubstituted allenes. In the experimental materials used by the author, we found Bis[(pinacolato)boryl]methane(cas: 78782-17-9Product Details of 78782-17-9)

Bis[(pinacolato)boryl]methane(cas: 78782-17-9) belongs to organoboron compounds. Organoboron compounds have been a cornerstone of synthetic transformations for decades. Areas such as boron-containing catalysts, metalate chemistry, photoredox methods, and boryl anions have brought significant new developments in understanding and provided new reactivity upon.Product Details of 78782-17-9

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In 2017,Edelstein, Emma K.; Namirembe, Sheila; Morken, James P. published 《Enantioselective Conjunctive Cross-Coupling of Bis(alkenyl)borates: A General Synthesis of Chiral Allylboron Reagents》.Journal of the American Chemical Society published the findings.Product Details of 78782-17-9 The information in the text is summarized as follows:

Pd-catalyzed conjunctive cross-coupling was used for the synthesis of enantioenriched allylboron reagents. This reaction employs nonsym. bis(alkenyl)borates as substrates and appears to occur by a mechanism that involves selective activation of the less substituted alkene followed by migration of the more substituted alkene during a Pd-induced metalate rearrangement.Bis[(pinacolato)boryl]methane(cas: 78782-17-9Product Details of 78782-17-9) was used in this study.

Bis[(pinacolato)boryl]methane(cas: 78782-17-9) belongs to organoboron compounds.Product Details of 78782-17-9 Organoboron compounds have been a cornerstone of synthetic transformations for decades. Areas such as boron-containing catalysts, metalate chemistry, photoredox methods, and boryl anions have brought significant new developments in understanding and provided new reactivity upon.

Referemce:
Alcohol – Wikipedia,
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Boyko, Yaroslav D.; Huck, Christopher J.; Ning, Shang; Shved, Alexander S.; Yang, Cheng; Chu, Tiffany; Tonogai, Emily J.; Hergenrother, Paul J.; Sarlah, David published an article in 2021. The article was titled 《Synthetic studies on selective, proapoptotic isomalabaricane triterpenoids aided by computational techniques》, and you may find the article in Journal of the American Chemical Society.COA of Formula: C13H26B2O4 The information in the text is summarized as follows:

The isomalabaricanes comprise a large family of marine triterpenoids with fascinating structures that have been shown to be selective and potent apoptosis inducers in certain cancer cell lines. In this article, we describe the successful total syntheses of the isomalabaricanes Stelletin A, Stelletin E, and Rhabdastrellic acid A, as well as the development of a general strategy to access other natural products within this unique family. High-throughput experimentation and computational chem. methods were used in this endeavor. A preliminary structure-activity relationship study of Stelletin A revealed the trans-syn-trans core motif of the isomalabaricanes to be critical for their cytotoxic activity. In addition to this study using Bis[(pinacolato)boryl]methane, there are many other studies that have used Bis[(pinacolato)boryl]methane(cas: 78782-17-9COA of Formula: C13H26B2O4) was used in this study.

Bis[(pinacolato)boryl]methane(cas: 78782-17-9) belongs to organoboron compounds. Organoboron compounds are versatile intermediates and as such are some of the most important classes of reagents in modern organic chemistry. This stems from their ease of preparation combined with their ability to undergo a broad range of chemical transformations.COA of Formula: C13H26B2O4

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Category: alcohols-buliding-blocksIn 2017 ,《Copper-catalyzed propargylation of diborylmethane》 appeared in Chemical Communications (Cambridge, United Kingdom). The author of the article were Li, Feng; Zhang, Zhen-Qi; Lu, Xi; Xiao, Bin; Fu, Yao. The article conveys some information:

A Cu/PPh3-catalyzed propargylic substitution reaction of diborylmethane is reported. Different substituted propargyl electrophiles can be employed in this reaction, and various synthetic valuable functional groups can be tolerated. Di-deuterated diborylmethane can also be used under these conditions and generates α-deuterated alkylboronic esters in good yield. In the experiment, the researchers used Bis[(pinacolato)boryl]methane(cas: 78782-17-9Category: alcohols-buliding-blocks)

Bis[(pinacolato)boryl]methane(cas: 78782-17-9) belongs to organoboron compounds.Category: alcohols-buliding-blocks Organoboron compounds have been a cornerstone of synthetic transformations for decades. Areas such as boron-containing catalysts, metalate chemistry, photoredox methods, and boryl anions have brought significant new developments in understanding and provided new reactivity upon.

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Computed Properties of C13H26B2O4In 2019 ,《Catalytic Enantioselective Boryl and Silyl Substitution with Trifluoromethyl Alkenes: Scope, Utility, and Mechanistic Nuances of Cu-F β-Elimination》 was published in Journal of the American Chemical Society. The article was written by Paioti, Paulo H. S.; del Pozo, Juan; Mikus, Malte S.; Lee, Jaehee; Koh, Ming Joo; Romiti, Filippo; Torker, Sebastian; Hoveyda, Amir H.. The article contains the following contents:

Catalytic enantioselective methods are introduced that allow access to a variety of allyl boronates and silanes that contain a difluoroalkene unit; the resulting products may be used for the preparation of organofluorine compounds in high enantiomeric purity. Also, a number of key mechanistic aspects of the transformations were studied and analyzed. Thus, 1st, an NHC-Cu-catalyzed method for boryl substitution with F3C-substituted alkenes is introduced. These processes, unlike the previously reported strategies, are applicable to alkyl as well as aryl substituted substrates, afford allyl boronates bearing a difluoroalkene moiety (up to 98% yield and 95:5 er). Second, the corresponding silyl substitutions, the 1st reported cases of their kind, are presented (up to 94% yield and 97:3 er). Third, exptl. and computational (DFT) studies are described that shed light on key mechanistic aspects of the catalytic processes. Evidence (x-ray structures of Cu-alkyl intermediates and kinetic studies) is put forth illustrating that the initial Cu-boryl and Cu-silyl addition is significantly faster than the ensuing Cu-F elimination, and that the latter step can be facilitated by either a mild Lewis acid (e.g., a Li or Na cation) or a nucleophilic promoter (e.g., an alkoxide). These findings together with DFT studies demonstrate that Cu-F β-elimination probably proceeds with anti-stereochem. Representative cases of ways through which the new mechanistic understanding may be used to rationalize previously disclosed findings, significantly improve a transformation, or develop new diastereo- and enantioselective catalytic methods are provided. For example, an explanation is provided regarding why bisphosphine-Cu complexes do not efficiently promote boryl substitutions with aryl-substituted substrates, but the corresponding silyl substitutions are facile, and how the size of a ligand can impact regioselectivity and efficiency. In the experiment, the researchers used many compounds, for example, Bis[(pinacolato)boryl]methane(cas: 78782-17-9Computed Properties of C13H26B2O4)

Bis[(pinacolato)boryl]methane(cas: 78782-17-9) belongs to organoboron compounds. Organoboron compounds are versatile intermediates and as such are some of the most important classes of reagents in modern organic chemistry. This stems from their ease of preparation combined with their ability to undergo a broad range of chemical transformations.Computed Properties of C13H26B2O4

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《Stereoselective Tandem Bis-Electrophile Couplings of Diborylmethane》 was written by Murray, Stephanie A.; Liang, Michael Z.; Meek, Simon J.. Product Details of 78782-17-9This research focused onthree component coupling diborylmethane epoxide allyl bromide preparation hydroxyboronate; diol hydroxyboronate chiral preparation stereoselective borylation ring opening epoxide. The article conveys some information:

A copper-catalyzed three-component linchpin coupling method for the stereoselective union of readily available epoxides R1R2C(O)CHR3 with diborylmethyl lithium (pinB)2CHLi and allyl electrophiles is disclosed; the reaction afforded borylated alc. derivatives R1R2C(OX)CH2CHBpinCH2CH:CH2 (X = TBSO, H) or the corresponding 1,3-diols R1R2C(OH)CH2CH(OH)CH2CH:CH2 after oxidation Transformations employ [B(pin)]2-methane as a conjunctive reagent, resulting in the formation of two C-C bonds at a single carbon center bearing a C(sp3) organoboron functional group. Products are obtained in 42-99% yield, and up to >20:1 dr. The utility of the approach is highlighted by stereospecific transformations entailing allylation, tandem cross coupling, and application to the synthesis 1,3-polyol motifs. In the experiment, the researchers used Bis[(pinacolato)boryl]methane(cas: 78782-17-9Product Details of 78782-17-9)

Bis[(pinacolato)boryl]methane(cas: 78782-17-9) belongs to organoboron compounds.Product Details of 78782-17-9 Organoboron compounds have been a cornerstone of synthetic transformations for decades. Areas such as boron-containing catalysts, metalate chemistry, photoredox methods, and boryl anions have brought significant new developments in understanding and provided new reactivity upon.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Wang, Lucia; Lin, Shengjia; Zhu, Yawei; Ferrante, Daniel; Ishak, Timaf; Baba, Yuki; Sharma, Abhishek published their research in Chemical Communications (Cambridge, United Kingdom) in 2021. The article was titled 《α-Hydroxy boron-enabled regioselective access to bifunctional halo-boryl alicyclic ethers and α-halo borons》.Electric Literature of C13H26B2O4 The article contains the following contents:

α-Hydroxy borons are an underused class of compounds and their only previous application involved oxidation into acylborons. Herein, the authors describe the synthesis of functionalized olefinic α-hydroxy borons and their utility to enable a novel and regioselective route to hitherto unknown bifunctional halo-boryl tetrahydrofurans/tetrahydropyrans and α-halo MIDA boronates. The orthogonally functionalized alicyclic ethers provided a building block-based approach for diversification of the THF core. In the experimental materials used by the author, we found Bis[(pinacolato)boryl]methane(cas: 78782-17-9Electric Literature of C13H26B2O4)

Bis[(pinacolato)boryl]methane(cas: 78782-17-9) belongs to organoboron compounds. Organoboron compounds have been a cornerstone of synthetic transformations for decades. Areas such as boron-containing catalysts, metalate chemistry, photoredox methods, and boryl anions have brought significant new developments in understanding and provided new reactivity upon.Electric Literature of C13H26B2O4

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Recommanded Product: Bis[(pinacolato)boryl]methaneIn 2017 ,《Base-promoted, deborylative secondary alkylation of N-heteroaromatic N-oxides with internal gem-bis[(pinacolato)boryl]alkanes: a facile derivatization of 2,2′-bipyridyl analogues》 appeared in Chemical Communications (Cambridge, United Kingdom). The author of the article were Hwang, Chiwon; Jo, Woohyun; Cho, Seung Hwan. The article conveys some information:

A base-promoted, secondary alkylation of N-heteroaromatic N-oxides, e.g., I using internal gem-bis[(pinacolato)boryl]alkanes R1R2C(Bpin)2 [R1 = H, CH3, (CH2)5CH3; R2 = CH3, CH2C6H5, CH2HC=CH2, etc.] as alkylation reagents is reported. The reaction exhibits a broad scope, providing deoxygenated secondary alkylated N-heteroaromatic compounds, e.g., II with high efficiency. The usefulness of the developed protocol is evidenced by the sequential direct alkylation of 2,2′-bipyridine-N-oxide. In the experimental materials used by the author, we found Bis[(pinacolato)boryl]methane(cas: 78782-17-9Recommanded Product: Bis[(pinacolato)boryl]methane)

Bis[(pinacolato)boryl]methane(cas: 78782-17-9) belongs to organoboron compounds. Organoboron compounds have been a cornerstone of synthetic transformations for decades. Areas such as boron-containing catalysts, metalate chemistry, photoredox methods, and boryl anions have brought significant new developments in understanding and provided new reactivity upon.Recommanded Product: Bis[(pinacolato)boryl]methane

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