331958-88-4

Usage

Chemical Family

2-(tetrahydrofuran-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane belongs to the boronic acid esters family.

Usage

It is commonly used as a reagent in organic synthesis.

Role in Organic Synthesis

It is particularly used in the formation of carbon-carbon and carbon-heteroatom bonds.

Specific Reaction

It is often used in Suzuki-Miyaura cross-coupling reactions.

Reactivity and Stability

It is valued for its high reactivity and stability.

Complex Formation

It easily forms complexes with various organic substrates, making it a versatile tool in the development of new pharmaceuticals, agrochemicals, and materials.

Medicinal Chemistry Potential

It is highly valued in the field of medicinal chemistry for its potential in the synthesis of biologically active compounds.

Upstream product

• 1191-99-7 2,3-dihydro-2H-furan 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 

Relevant academic research and scientific papers

Combining high pressure and catalysis: Pinacol- or catecholborane hydroboration of functionalized olefins

The hydroboration of three families of functionalized olefins (1-bromo- and 1,3-dibromopropenes, allylamines, 2,3-dihydrofuran) by pinacolborane and catecholborane has been studied under various experimental conditions. For 1-bromo- and 1,3-dibromopropenes, pinacolborane (PBH) is a poor reagent that requires the use of high pressure in ethereal solvents and provides only by-products, resulting from the undesired β-bromoboronate regioisomer. By contrast, catecholborane (CBH) affords mainly the expected α-bromoboronate at atmospheric pressure. With dibenzylallylamine, PBH yields a mixture of the two possible regioisomers (β- and γ-amino-boronates), whatever the pressure, while CBH affords selectively the expected γ-isomer in good yields under atmospheric thermal conditions. For 2,3-dihydrofuran, only PBH gives an efficient access, in THF, to a mixture of the corresponding α- and β-regioisomers when combining the effects of 0.5% Wilkinson's catalyst and high pressure.

Combining high pressure and catalysis: Pinacol- or catecholborane hydroboration of functionalized olefins

The hydroboration of three families of functionalized olefins (1-bromo- and 1,3-dibromopropenes, allylamines, 2,3-dihydrofuran) by pinacolborane and catecholborane has been studied under various experimental conditions. For 1-bromo- and 1,3-dibromopropenes, pinacolborane (PBH) is a poor reagent that requires the use of high pressure in ethereal solvents and provides only by-products, resulting from the undesired β-bromoboronate regioisomer. By contrast, catecholborane (CBH) affords mainly the expected α-bromoboronate at atmospheric pressure. With dibenzylallylamine, PBH yields a mixture of the two possible regioisomers (β- and γ-aminoboronates), whatever the pressure, while CBH affords selectively the expected γ-isomer in good yields under atmospheric thermal conditions. For 2,3-dihydrofuran, only PBH gives an efficient access, in THF, to a mixture of the corresponding α- and β-regioisomers when combining the effects of 0.5% Wilkinson's catalyst and high pressure. The Royal Society of Chemistry 2000.