1131912-76-9

Usage

Uses

Used in Pharmaceutical Industry:
Tetrahydropyran-4-boronic acid pinacol ester serves as a key intermediate in the synthesis of various pharmaceutical compounds. Its reactivity in cross-coupling reactions allows for the creation of complex molecular structures that are essential for developing new drugs with specific therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical sector, Tetrahydropyran-4-boronic acid pinacol ester is utilized as a precursor for the synthesis of bioactive molecules with pesticidal or herbicidal properties. Its ability to form carbon-carbon bonds through cross-coupling reactions contributes to the development of novel agrochemicals with improved efficacy and selectivity.
Used in Organic Synthesis:
Tetrahydropyran-4-boronic acid pinacol ester is employed as a versatile building block in organic synthesis for constructing a wide range of organic molecules. Its stability and reactivity make it suitable for various synthetic routes, including the formation of complex natural products and the synthesis of advanced materials.
Used in Research and Development:
Tetrahydropyran-4-boronic acid pinacol ester is also used in academic and industrial research settings to explore new synthetic methodologies and to develop innovative applications in chemical biology and materials science. Its unique properties make it an attractive candidate for studying reaction mechanisms and developing new catalytic systems.

Upstream product

• 25637-16-5 4-bromotetrahydro-2H-pyran 
• 73183-34-3 bis(pinacol)diborane 
• 142-68-7 TETRAHYDROPYRANE 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 25637-18-7 4-iodotetrahydropyran 
• 13826-27-2 2,2'-bis(1,3,2-benzodioxaborole) 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 592-41-6 1-hexene 
• 274-07-7 benzo[1,3,2]dioxaborole 
• 1768-64-5 4-chlorotetrahydro-2H-pyran 
• 40191-32-0 tetrahydro-2H-pyran-4-carbonylchloride 
• 38041-19-9 4-aminotetrahydropyran 
• 5337-03-1 tetrahydro-2H-pyran-4-carboxylic acid 

Downstream Products

• 1394939-90-2 4-[4-(3-nitrophenyl)-2-(tetrahydro-2H-pyran-4-yl)-1,3-thiazol-5-yl]pyridine 

Relevant academic research and scientific papers

A Copper(I)-Catalyzed Radical-Relay Reaction Enabling the Intermolecular 1,2-Alkylborylation of Unactivated Olefins

The first catalytic intermolecular 1,2-alkylborylation reaction via a radical-relay mechanism between unactivated olefins, bis(pinacolato)diboron, and an alkyl electrophile is reported. Successful implementation of this method requires that the competing boryl substitution of the alkyl electrophile is retarded to facilitate the radical relay. This challenge was overcome using electronically or sterically demanding alkyl electrophiles, which results in the simultaneous and highly regioselective introduction of a gem-difluoro, monofluoro, tertiary, or secondary alkyl group and a boryl group across the C=C double bond.

Transition-Metal-Free Borylation of Alkyl Iodides via a Radical Mechanism

We describe an operationally simple transition-metal-free borylation of alkyl iodides. This method uses commercially available diboron reagents as the boron source and exhibits excellent functional group compatibility. Furthermore, a diverse range of prim

Zinc-catalyzed borylation of primary, secondary and tertiary alkyl halides with alkoxy diboron reagents at room temperature

A new catalytic system based on a ZnII NHC precursor has been developed for the cross-coupling reaction of alkyl halides with diboron reagents, which represents a novel use of a Group XII catalyst for C=X borylation. This approach gives borylations of unactivated primary, secondary, and tertiary alkyl halides at room temperature to furnish alkyl boronates, with good functional-group compatibility, under mild conditions. Preliminary mechanistic investigations demonstrated that this borylation reaction seems to involve one-electron processes. Coupling a la carte: A catalytic system based on a ZnII N-heterocyclic carbene precursor has been developed for the cross-coupling reaction of alkyl halides with diboron reagents (see scheme). This is a novel use of a Group 12 catalyst for C=X borylation. IMes=1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene. Copyright

Metal-Free Radical Borylation of Alkyl and Aryl Iodides

A metal-free radical borylation of alkyl and aryl iodides with bis(catecholato)diboron (B2cat2) as the boron source under mild conditions is introduced. The borylation reaction is operationally easy to conduct and shows high functional group tolerance and broad substrate scope. Radical clock experiments and density functional theory calculations provide insights into the mechanism and rate constants for C-radical borylation with B2cat2 are disclosed.

Photoinduced decarboxylative borylation of carboxylic acids

The conversion of widely available carboxylic acids into versatile boronic esters would be highly enabling for synthesis. We found that this transformation can be effected by illuminating the N-hydroxyphthalimide ester derivative of the carboxylic acid under visible light at room temperature in the presence of the diboron reagent bis(catecholato)diboron. A simple workup allows isolation of the pinacol boronic ester. Experimental evidence suggests that boryl radical intermediates are involved in the process. The methodology is illustrated by the transformation of primary, secondary, and tertiary alkyl carboxylic acids as well as a diverse range of natural-product carboxylic acids, thereby demonstrating its broad utility and functional group tolerance.

Cu-Catalyzed Decarboxylative Borylation

A simple method for the conversion of carboxylic acids to boronic esters via redox-active esters (RAEs) is reported using copper catalysis. The scope of this transformation is broad, and compared with the known protocols available, it represents the most inexpensive, rapid, and operationally simple option. In addition to a full exploration of the scope, a kinetic study was performed to elucidate substrate and reagent concentration dependences.

Chromium-Catalyzed Borylative Coupling of Aliphatic Bromides with Pinacolborane by Hydrogen Evolution

The chromium-catalyzed borylative coupling between aliphatic bromides and pinacolborane (HBpin) is described. This reaction was promoted by low-cost and bench-stable CrCl3as a precatalyst combined with 4,4′-di-tert-butyl-2,2′-dipyridyl and aluminum, presenting a rare example of using HBpin as a borane reagent by coupling with alkyl bromides in forming borylated alkanes. Mechanistic studies indicate that aluminum plays important roles in the formation of reactive Cr species and aliphatic radicals, which lead to (alkyl)Cr by reaction with HBpin to give the products.

Electrochemical Borylation of Alkyl Halides: Fast, Scalable Access to Alkyl Boronic Esters

Herein, a fast, scalable, and transition-metal-free borylation of alkyl halides (X = I, Br, Cl) enabled by electroreduction is reported. This process provides an efficient and practical access to primary, secondary, and tertiary boronic esters at a high current. More than 70 examples, including the late-stage borylation of natural products and drug derivatives, are furnished at room temperature, thereby demonstrating the broad utility and functional-group tolerance of this protocol. Mechanistic studies disclosed that B2cat2 serves as both a reagent and a cathodic mediator, enabling electroreduction of difficult-to-reduce alkyl bromides or chlorides at a low potential.

Transition metal- And light-free radical borylation of alkyl bromides and iodides using silane

We report operationally simple and neutral conditions for borylation of alkyl bromides and iodides to alkyl boronic esters under transition metal- and light-free conditions. A series of substrates with a wide range of functional groups were effectively transformed into the borylation products in moderate to good yields. Mechanistic studies, including radical clock experiments and DFT calculations, gave detailed insight into the radical borylation process.

Method for directly preparing alkyl borate compound from alkyl halide

The invention relates to a method for directly preparing an alkyl borate compound from an alkyl halide, which comprises the following steps: in a protective atmosphere, mixing a titanium metal catalyst, an alkali compound, a borate compound and an alkyl halide or sulfonate compound, reacting at 35-100 DEG C for 8-24 hours, so that the alkyl halide or sulfonate compound is directly converted into the alkyl boronic acid pinacol ester compound. The method is simple to operate, low in cost, good in functional group tolerance and wide in substrate application range.