37490-32-7

Usage

Uses

Used in Organic Synthesis:
(E)-5-CHLORO-1-PENTENEBORONIC ACID is used as a reagent in organic synthesis for its ability to participate in Suzuki-Miyaura cross-coupling reactions. These reactions are widely utilized in the synthesis of complex organic molecules, making it a valuable tool in this field.
Used in Pharmaceutical and Agrochemical Preparation:
In the pharmaceutical industry, (E)-5-CHLORO-1-PENTENEBORONIC ACID is used as a building block for the preparation of various pharmaceuticals. Its unique structure and reactivity contribute to the development of new and effective drugs.
Similarly, in the agrochemical industry, (E)-5-CHLORO-1-PENTENEBORONIC ACID is used as a building block for the preparation of agrochemicals. Its properties allow for the creation of new compounds with potential applications in agriculture, such as pesticides and herbicides.
Used in Medicinal Chemistry Research:
(E)-5-CHLORO-1-PENTENEBORONIC ACID is used as a research tool in medicinal chemistry due to its unique structure and reactivity. It aids in the exploration of new chemical pathways and the development of innovative therapeutic agents.
Used in Material Science Research:
In the field of material science, (E)-5-CHLORO-1-PENTENEBORONIC ACID is used for its potential applications in the development of new materials with specific properties. Its reactivity and structural features make it a valuable component in the design and synthesis of advanced materials.

InChI:InChI=1/C5H10BClO2/c7-5-3-1-2-4-6(8)9/h2,4,8-9H,1,3,5H2/b4-2+

Upstream product

• 55671-55-1 dibromoborane dimethylsulfide 
• 14267-92-6 1-chloro-4-pentyne 
• 7732-18-5 water 
• 126688-98-0 B-2-(E)-(5-chloropent-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 1428541-20-1 (E)-(5-chloropent-1-en-1-yl)(o-tolyl)-λ³-iodanyl trifluoromethanesulfonate 
• 1613511-02-6 (E)-N-(5-chloropent-1-en-1-yl)benzamide 
• 16424-50-3 (E)-(5-chloropent-1-en-1-yl)benzene 

Relevant academic research and scientific papers

A relay catalysis strategy for enantioselective nickel-catalyzed migratory hydroarylation forming chiral α-aryl alkylboronates

Ligand-controlled reactivity plays an important role in transition-metal catalysis, enabling a vast number of efficient transformations to be discovered and developed. However, a single ligand is generally used to promote all steps of the catalytic cycle (e.g., oxidative addition, reductive elimination), a requirement that makes ligand design challenging and limits its generality, especially in relay asymmetric transformations. We hypothesized that multiple ligands with a metal center might be used to sequentially promote multiple catalytic steps, thereby combining complementary catalytic reactivities through a simple combination of simple ligands. With this relay catalysis strategy (L/L?), we report here the first highly regio- and enantioselective remote hydroarylation process. By synergistic combination of a known chain-walking ligand and a simple asymmetric cross-coupling ligand with the nickel catalyst, enantioenriched α-aryl alkylboronates could be rapidly obtained as versatile synthetic intermediates through this formal asymmetric remote C(sp3)-H arylation process.

Copper-catalyzed oxyvinylation of diazo compounds

A copper(I)-catalyzed vinylation of diazo compounds with vinylbenziodoxolone reagents (VBX) as partners is reported. The transformation tolerates diverse functionalities on both reagents delivering polyfunctionalized vinylated products. The strategy was successfully extended to a three-component/intermolecular version with alcohols. The obtained products contain synthetically versatile functional groups, such as an aryl iodide, an ester, and an allylic leaving group, enabling further modification.

Copper-Catalyzed Oxy-Alkenylation of Homoallylic Alcohols to Generate Functional syn-1,3-Diol Derivatives

A novel method for the synthesis of a wide range of functionalized 1,3-diol derivatives is reported. Employing a copper-catalyzed oxy-alkenylation strategy, a range of readily available, substituted homoallylic alcohol derivatives and alkenyl(aryl) iodonium salts combine to form syn-1,3-carbonates in excellent yield and with high selectivity. Furthermore, the products formed are amenable to an iterative reaction sequence, thus affording highly complex polyketide-like fragments. Polyols: The reported copper-catalyzed oxy-alkenylation strategy works well for a range of readily available, substituted homoallylic alcohol derivatives and alkenyl(aryl) iodonium salts to form syn-1,3-carbonates in excellent yield and high selectivity. Furthermore, the products formed are amenable to an iterative reaction sequence, thus affording highly complex polyketide-like fragments.

Rhodium(III)-catalyzed cross-coupling of alkenylboronic acids and N -pivaloyloxylamides

Rh(III)-catalyzed umpolung amidation of alkenylboronic acids for the synthesis of enamides is reported. This reaction proceeds readily at room temperature and displays an extremely wide spectrum of functional group tolerance. With cooperation of hydrobora

Copper-catalyzed electrophilic carbofunctionalization of alkynes to highly functionalized tetrasubstituted alkenes

Copper catalysts enable the electrophilic carbofunctionalization of alkynes with vinyl- and diaryliodonium triflates. The new process forms highly substituted alkenyl triflates from a range of alkynes via a pathway that is opposite to classical carbometalation. The alkenyl triflate products can be elaborated through cross-coupling reactions to generate synthetically useful tetrasubstituted alkenes

Dichloroborane-dioxane: An exceptional reagent for the preparation of alkenyl- and alkylboronic acids

Terminal alkynes and alkenes were conveniently hydroborated to the corresponding alkenyl- and alkyldichloroboranes using dichloroborane-dioxane in dichloromethane. These dichloroboranes were hydrolyzed by water to the corresponding alkenyl- and alkylboron