126726-62-3

Usage

Uses

Used in Organic Synthesis:
Isopropenylboronic acid pinacol ester is used as an intermediate for the synthesis of a variety of cyclic and acyclic organic compounds, providing a foundation for the creation of complex molecular structures.
Used in Suzuki-Miyaura Cross-Coupling Reactions:
In the field of organic chemistry, Isopropenylboronic acid pinacol ester is used as a reagent for palladium-catalyzed Suzuki-Miyaura cross-coupling reactions, enabling the formation of carbon-carbon bonds and the synthesis of biaryl compounds.
Used in Inverse-Electron-Demand Diels-Alder Reaction:
Isopropenylboronic acid pinacol ester is utilized as a reagent in inverse-electron-demand Diels-Alder reactions, allowing for the construction of six-membered rings and the synthesis of various complex organic molecules.
Used in Simmons-Smith Cyclopropanation Reaction:
This ester reagent is used in Simmons-Smith cyclopropanation reactions, which are crucial for the formation of cyclopropane rings in organic molecules.
Used in Polyene Cyclization:
Isopropenylboronic acid pinacol ester is employed as a reagent in polyene cyclization reactions, contributing to the synthesis of cyclic polyene compounds.
Used in Stereoselective Aldol Reactions:
As a reagent in stereoselective aldol reactions, Isopropenylboronic acid pinacol ester helps in the formation of carbon-carbon bonds with controlled stereochemistry, which is essential for the synthesis of enantiomerically pure compounds.
Used in Grubbs Cross-Metathesis Reaction:
This ester reagent is used in Grubbs cross-metathesis reactions, facilitating the exchange of olefinic bonds between molecules and enabling the synthesis of new compounds with unique structures.
Used in Intramolecular Suzuki-Miyaura Reaction:
Isopropenylboronic acid pinacol ester is used as a reagent in intramolecular Suzuki-Miyaura reactions, allowing for the formation of cyclic compounds through the coupling of molecular fragments.
Used in Stereoselective Cross-Metathesis:
This ester reagent is employed in stereoselective cross-metathesis reactions, enabling the synthesis of compounds with specific stereochemistry.
Used in Dipolar Cycloaddition:
Isopropenylboronic acid pinacol ester is used as a reagent in dipolar cycloaddition reactions, contributing to the formation of five-membered heterocyclic compounds.
Used in Iodosulfonylation:
This ester reagent is utilized in iodosulfonylation reactions, which are important for the introduction of sulfonyl groups into organic molecules.
Used in Asymmetric Conjugate Addition and Intramolecular Hydroacylation:
Isopropenylboronic acid pinacol ester is used as a reagent in asymmetric conjugate addition and intramolecular hydroacylation reactions, allowing for the synthesis of enantiomerically pure compounds with potential applications in various industries.
Used in Pharmaceutical Industry:
Isopropenylboronic acid pinacol ester is used as a reagent in the preparation of various therapeutic kinase and enzymatic inhibitors, playing a crucial role in the development of new drugs for the treatment of various diseases.

Sources

https://www.sigmaaldrich.com/catalog/product/aldrich/663212?lang=en®ion=US https://www.trc-canada.com/product-detail/?I821825

InChI:InChI=1/C9H17BO2/c1-7(2)10-11-8(3,4)9(5,6)12-10/h1H2,2-6H3

Upstream product

• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 14559-87-6 isopropenylboronic acid 
• 557-93-7 2-bromoprop-1-ene 
• 28049-80-1 bis(diisopropylamino)chloroborane 
• 13826-27-2 2,2'-bis(1,3,2-benzodioxaborole) 
• 67-64-1 acetone 
• 201733-56-4 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane 
• 73183-34-3 bis(pinacol)diborane 

Downstream Products

• 1067191-60-9 N-[4-(cyano-dimethyl-methyl)-3-isopropenyl-phenyl]-3,4-dimethoxy-benzamide 
• 1071497-55-6 8-fluoro-2-isopropenyl-4-methyl-3-(4-pyrazol-1-ylbenzyl)quinolin-5-ol 
• 1071497-60-3 8-chloro-2-isopropenyl-4-methyl-3-(4-pyrazol-1-ylbenzyl)quinolin-5-ol 
• 1140897-36-4 3-(1-(4-chlorophenyl)cyclopropyl)-8-(prop-1-en-2-yl)-[1,2,4]triazolo[4,3-a]pyridine trifluoroacetate 
• 1186637-51-3 3-chloro-5-(prop-1-en-2-yl)picolinonitrile 
• 1228450-93-8 1-cyclohexyl-3-[7-isopropenyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea 
• 1238893-92-9 4-(prop-1-en-2-yl)-5-[4-(trifluoromethyl)phenyl]oxazole 
• 1232038-38-8 C₂₅H₂₂ClN₇O 
• 1160682-64-3 Methyl 2-amino-5-(1-methylethenyl)-6-(methyloxy)-3-nitrobenzoate 
• 1257231-24-5 2-acetoxy-7-benzyloxy-3-(prop-1-en-2-yl)naphthalene 
• 1360903-34-9 (R)-3-(2-methoxyphenyl)-4-methylpent-4-enal 
• 1360903-33-8 (R)-4-methyl-3-phenylpent-4-enal 
• 90433-90-2 methyl 4-(prop-1-en-2-yl)-1H-pyrrole-2-carboxylate 
• 1395284-39-5 methyl 6-(2,6-difluoro-4-(prop-1-en-2-yl)phenyl)-5-fluoropicolinate 

Relevant academic research and scientific papers

Synthesis method of isopropenyl boronic acid pinacol ester

The invention discloses a synthesis method of isopropenyl boronic acid pinacol ester. The synthesis method comprises the following steps: generating a gem-diboronation product from acetone and biborate under the action of a copper carbene reagent, then carrying out elimination reaction in the presence of p-toluenesulfonic acid, and finally, subjecting the product and pinacol to a one-pot-process reaction to obtain the isopropenyl boronic acid pinacol ester. The method is simple to operate, the boronation reaction is directly carried out under the action of a metal copper catalyst, the use of 2-bromopropylene in a traditional process is avoided, and a new synthesis path is provided for the synthesis of the isopropenyl boronic acid pinacol ester.

Visible-light-mediated borylation of aryl and alkyl halides with a palladium complex

Palladium catalyzed visible-light-mediated borylation of inactivated aryl and alkyl halides is reported; the method provided high yields and excellent functional group compatibility. Furthermore, arylsilicates were synthesized selectively using dimethylphenylsilyl boronic ester via changing the reaction conditions. Finally, the possible reaction mechanism is determined through fluorescence quenching and turn on/off experiments.

Method for synthetizing isopropenyl boric acid ester

The invention discloses a method for synthetizing isopropenyl boric acid ester. Acetone is used as a raw material and subjected to a reaction with hydrazine hydrate to generate hydrazone, then, isopropenyl halogen is generated at the existence of NXS and organic base and then subjected to a one-pot reaction with metallic lithium and bi(disopropylamine) boron halide, diol and a polymerization inhibitor are added for a backflow reaction to obtain isopropenyl boronic acid ester, and the yield is 65-69%,. The method is easy and convenient to implement, purification is convenient, the yield is high, no ultralow temperature reaction is needed, and the method is suitable for industrial enlarged production.

Oxidative palladium(II) catalysis: A highly efficient and chemoselective cross-coupling method for carbon-carbon bond formation under base-free and nitrogenous-ligand conditions

We report herein the development of a general and mild protocol of oxygen-promoted Pd(II) catalysis resulting in the selective cross-couplings of alkenyl- and arylboron compounds with various olefins. Unlike most cross-coupling reactions, this new methodology works well even in the absence of bases, consequently averting undesired homo-couplings. Nitrogen-based ligands including dimethyl-phenanathroline enhance reactivities and offer a highly efficient and stereoselective methodology to overcome challenging substrate limitations. For instance, oxidative palladium(II) catalysis is effective with highly substituted alkenes and cyclic alkenes, which are known to be incompatible with other known catalytic conditions. Most examined reactions progressed smoothly to completion at low temperatures and in short times. These interesting results provide mechanistic insights and utilities for a new paradigm of palladium catalytic cycles without bases.

Oxygen-promoted palladium(II) catalysis: Facile C(sp2)-C(sp 2) bond formation via cross-coupling of alkenylboronic compounds and olefins

(Chemical Equation Presented) Oxygen-promoted Pd(II) catalysis facilitated the synthesis of conjugated dienes by cross-coupling of alkenylboronic compounds and various olefins including highly substituted alkenes and cyclohexenone. Under mild conditions, these versatile reactions were efficient and highly stereoselective.