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Usage

Uses

Used in Pharmaceutical Industry:
(E)-2-Cyclopropylvinylboronic acid is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure allows for the formation of complex organic molecules, making it an important tool in the development of new drugs.
Used in Agrochemical Industry:
(E)-2-Cyclopropylvinylboronic acid is used as a building block in the production of agrochemicals. Its reactivity and unique structure enable the creation of new compounds with potential applications in agriculture.
Used in Material Science:
(E)-2-Cyclopropylvinylboronic acid is used as a component in the development of new materials. Its ability to form carbon-carbon bonds through the Suzuki-Miyaura coupling reaction makes it a valuable asset in the creation of advanced materials with specific properties.
Used in Organic Synthesis:
(E)-2-Cyclopropylvinylboronic acid is used as a reagent in organic synthesis, particularly for the Suzuki-Miyaura coupling reaction. This reaction is a widely used method for forming carbon-carbon bonds, making (E)-2-Cyclopropylvinylboronic acid an essential tool in the creation of complex organic molecules in the laboratory.

Upstream product

• 849061-99-0 (E)-4,4,5,5-tetramethyl-2-(cyclopropyl-1-ethenyl)-1,3,2-dioxaborolane 
• 6746-94-7 Cyclopropylacetylene 
• 274-07-7 benzo[1,3,2]dioxaborole 

Relevant academic research and scientific papers

Synthesis of α-Borylated Ketones by Regioselective Wacker Oxidation of Alkenylboronates

As part of a program aimed at metal-catalyzed oxidative transformations of molecules with carbon-metalloid bonds, the synthesis of α-borylated ketones is reported via regioselective TBHP-mediated Wacker-type oxidation of N-methyliminodiacetic acid (MIDA)-protected alkenylboronates. The observed regioselectivity correlates with the hemilabile nature of the B-N dative bond in the MIDA boronate functional group, which allows boron to guide selectivity through a neighboring group effect.

Mild Base Promoted Nucleophilic Substitution of Unactivated sp3-Carbon Electrophiles with Alkenylboronic Acids

Diverse alkenylboronic acids react smoothly with various sp3-carbon electrophiles such as unactivated alkyl triflates in the presence of mild bases such as K3PO4. The reaction protocol is very mild and thereby enables high functional group tolerance. This transition metal-free condition is orthogonal towards the classic transition metal catalyzed Suzuki coupling. (Figure presented.).

Oxalyl Boronates Enable Modular Synthesis of Bioactive Imidazoles

Described herein is the preparation of oxalyl boronate building blocks and their application for the construction of heterocycles. The oxalyl unit, readily accessible through commercially available starting materials, enables a modular approach for the synthesis of imidazoles. A variety of aromatic, heteroaromatic, and alkyl carboxaldehydes were condensed with oxalyl boronates to afford substituted boryl imidazoles in a regiocontrolled fashion. Subsequent palladium-catalyzed cross-coupling with haloarenes furnished the desired trisubstituted imidazole scaffolds. To demonstrate the utility of these scaffolds, potent inhibitors of the serine/threonine-protein kinase STK10 were synthesized.

Preparation of α-imino aldehydes by [1,3]-rearrangements of O-alkenyl oximes

The synthesis of α-imino aldehydes has been achieved through the thermal [1,3]-rearrangement of O-alkenyl benzophenone oximes. A copper-mediated C-O bond coupling between benzophenone oxime and alkenyl boronic acids provides facile access to the required O-alkenyl oximes and a Horner-Wadsworth-Emmons olefination can be applied to the α-imino aldehyde products to give γ-imino-α,β-unsaturated esters. The scope of the method is described and mechanistic experiments are discussed.