75927-49-0 Usage
Description
Pinacol vinylboronate is an organoboron compound that serves as a versatile reagent and building block in organic synthesis. It is characterized by its ability to participate in various cross-coupling reactions, making it a valuable tool for the construction of complex organic molecules.
Uses
Used in Suzuki Reaction:
Pinacol vinylboronate is used as a reagent in Suzuki-Miyaura coupling reactions for the formation of carbon-carbon bonds between an organoboron compound and an organic halide or triflate.
Used in Mizoroki-Heck Reactions:
Pinacol vinylboronate is used as a reagent in Mizoroki-Heck reactions (cascade reaction) for the formation of alkenes through the coupling of an organoboron compound with an alkene.
Used in Intramolecular Nozaki-Hiyama-Kishi Reactions:
Pinacol vinylboronate is used as a reagent in intramolecular Nozaki-Hiyama-Kishi reactions for the formation of cyclic compounds through the coupling of an organoboron compound with an aldehyde or ketone.
Used in Stereoselective Cu-Catalyzed γ-Selective and Stereospecific Coupling:
Pinacol vinylboronate is used as a reagent in stereoselective Cu-catalyzed γ-selective and stereospecific coupling reactions for the formation of specific geometric isomers of alkenes.
Used in Control of Stereoselectivity and Mechanistic Portrait on Intramolecular (4+1)-Cycloaddition of Dialkoxycarbenes:
Pinacol vinylboronate is used as a reagent in the control of stereoselectivity and mechanistic portrait on intramolecular (4+1)-cycloaddition of dialkoxycarbenes for the formation of complex cyclic compounds.
Used in Regioand Stereoselective Synthesis of Trisubstituted Alkenes:
Pinacol vinylboronate is used as a reagent in the regioand stereoselective synthesis of trisubstituted alkenes via gold(I)-catalyzed hydrophosphoryloxylation of haloalkynes followed by Pd-catalyzed consecutive cross-coupling reactions.
Used in Asymmetric Birch Reductive Alkylation:
Pinacol vinylboronate is used as a reagent in asymmetric Birch reductive alkylation for the formation of chiral amines through the coupling of an organoboron compound with an aldehyde or ketone.
Used in Preparation of Molecular Tubes for Lipid Sensing:
Pinacol vinylboronate is used as a reagent in the preparation of molecular tubes for lipid sensing, enabling the detection and analysis of lipids in biological systems.
Used in Enzymatic Inhibitors, Antibiotics, Receptor Analogs, and Other Biologically Significant Compounds:
Pinacol vinylboronate is used as a reagent in the synthesis of enzymatic inhibitors, antibiotics, receptor analogs, and other biologically significant compounds, including their total syntheses, for various pharmaceutical and therapeutic applications.
Check Digit Verification of cas no
The CAS Registry Mumber 75927-49-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,5,9,2 and 7 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 75927-49:
(7*7)+(6*5)+(5*9)+(4*2)+(3*7)+(2*4)+(1*9)=170
170 % 10 = 0
So 75927-49-0 is a valid CAS Registry Number.
InChI:InChI=1/C8H16BO3/c1-6-9(11)12-8(4,5)7(2,3)10/h6,10H,1H2,2-5H3/q-1
75927-49-0Relevant articles and documents
An Olefinic 1,2-Boryl-Migration Enabled by Radical Addition: Construction of gem-Bis(boryl)alkanes
Zhao, Binlin,Li, Zexian,Wu, Yixiao,Wang, Yandong,Qian, Jiasheng,Yuan, Yu,Shi, Zhuangzhi
supporting information, p. 9448 - 9452 (2019/08/07)
A series of in situ formed alkenyl diboronate complexes from alkenyl Grignard reagents (commercially available or prepared from alkenyl bromides and Mg) with B2Pin2 (bis(pinacolato)diboron) react with diverse alkyl halides by a Ru photocatalyst to give various gem-bis(boryl)alkanes. Alkyl radicals add efficiently to the alkenyl diboronate complexes, and the adduct radical anions undergo radical-polar crossover, specifically, a 1,2-boryl-anion shift from boron to the α-carbon sp2 center. This transformation shows good functional-group compatibility and can serve as a powerful synthetic tool for late-stage functionalization in complex compounds. Measurements of the quantum yield reveal that a radical-chain mechanism is operative in which the alkenyl diboronates acts as reductive quencher for the excited state of the photocatalyst.
Synthesis of functionalized vinyl boronates via ruthenium-catalyzed olefin cross-metathesis and subsequent conversion to vinyl halides
Morrill, Christie,Grubbs, Robert H.
, p. 6031 - 6034 (2007/10/03)
Functionalized vinyl pinacol boronates suitable for Suzuki cross-coupling reactions are synthesized using ruthenium-catalyzed olefin cross-metathesis of 1-propenyl pinacol boronate and various alkenes, including functionalized and 1,1-disubstituted alkenes. The resultant boronate cross products are stereoselectively transformed into predominantly Z-vinyl bromides and E-vinyl iodides. The vinyl bromides may be synthesized in a two-step, one-pot synthesis from a variety of olefins, resulting in a Z-selective formal vinyl bromide cross-metathesis reaction.