1344115-77-0

Usage

Uses

Used in Organic Synthesis:
2-(cyclopropylmethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is used as a reagent in Suzuki-Miyaura cross-coupling reactions for the formation of complex organic molecules. Its cyclopropylmethyl group provides stability, while the tetramethyl substituents contribute to its reactivity, making it a valuable component in the synthesis process.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 2-(cyclopropylmethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is used as a key intermediate for the development of new drugs. Its selective reactivity and compatibility with a broad range of functional groups allow for the creation of diverse pharmaceutical compounds with potential therapeutic applications.
Used in Agrochemical Synthesis:
Similarly, in agrochemical synthesis, 2-(cyclopropylmethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is employed as a crucial building block for the production of various agrochemicals. Its stability and reactivity facilitate the synthesis of effective compounds for agricultural applications, such as pesticides and herbicides.

Upstream product

• 75-11-6 diiodomethane 
• 72824-04-5 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 927-73-1 3-butenyl chloride 
• 73183-34-3 bis(pinacol)diborane 
• 5162-44-7 1-bromo-4-butene 
• 7766-51-0 4-iodobut-1-ene 
• 778-29-0 but-3-enyl 4-methylbenzenesulfonate 
• 7051-34-5 cyclopropylcarbinyl bromide 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 13826-27-2 2,2'-bis(1,3,2-benzodioxaborole) 

Downstream Products

• 1344115-91-8 C₁₃H₁₆ 
• 1344115-93-0 C₁₃H₁₇Cl 
• 123186-25-4 1-(2-phenylethyl)-4-penten-1-ol 
• 2516-33-8 Cyclopropylmethanol 

Relevant academic research and scientific papers

Manganese(III)-Promoted Double Carbonylation of Anilines Toward α-Ketoamides Synthesis

Employing anilines as nucleophiles in double carbonylation is a longstanding challenge. In this communication, a Mn(III)-promoted double carbonylation of alkylborates or Hantzsch esters with anilines toward the synthesis of α-ketoamides has been developed. By using easily available potassium alkyltrifluoroborates or Hantzsch esters as the starting material, and cheap and non-toxic Mn(OAc)3 ? 2H2O as the promotor, a broad range of alkyl α-ketoamide derivatives were synthesized in moderate to good yields with excellent selectivity. (Figure presented.).

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.

TRANSGLUTAMINASE 2 (TG2) INHIBITORS

Described herein are compounds and pharmaceutical compositions containing such compounds which inhibit transglutaminase 2 (TG2). Also described herein are methods for using such TG2 inhibitors, alone or in combination with other compounds, for treating diseases or conditions that would benefit from TG2 inhibition.

Intermolecular Radical Addition to Ketoacids Enabled by Boron Activation

The intermolecular radical addition to the carbonyl group is difficult due to the facile fragmentation of the resulting alkoxyl radical. To date, the intermolecular radical addition to ketones, a valuable approach to construct quaternary carbon centers, remains a formidable synthetic challenge. Here, we report the first visible-light-induced intermolecular alkyl boronic acid addition to α-ketoacids enabled by the Lewis acid activation. The in situ boron complex formation is confirmed by various spectroscopic measurements and mechanistic probing experiments, which facilitates various alkyl boronic acid addition to the carbonyl group and prevents the cleavage of the newly formed C-C bond. Diversely substituted lactates can be synthesized from readily available alkyl boronic acids and ketoacids at room temperature merely under visible light irradiation, without any additional reagent. This boron activation approach can be extended to alkyl dihydropyridines as radical precursors with external boron reagents for primary, secondary, and tertiary alkyl radical additions. The pharmaceutically useful anticholinergic precursors are easily scaled up in multigrams under metal-free conditions in flow reactors.

Highly efficient synthesis of alkylboronate esters via Cu(II)-Catalyzed borylation of unactivated alkyl bromides and chlorides in air

A copper(II)-catalyzed borylation of alkyl halides with bis(pinacolato)diboron (B2pin2) has been developed, which can be carried out in air, providing a wide range of primary, secondary, and some tertiary alkylboronates in high yields. A variety of functional groups are tolerated and the protocol is also applicable to unactivated alkyl chlorides (including 1,1- and 1,2-dichlor-ides). Preliminary mechanistic investigations show that this borylation reaction involves one-electron processes.

Manganese-Catalyzed Borylation of Unactivated Alkyl Chlorides

The use of low-cost manganese(II) bromide (MnBr2) and tetramethylethylenediamine (TMEDA) catalyzes the cross coupling of (bis)pinacolatodiboron with a wide range of alkyl halides, demonstrating the first manganese-catalyzed coupling with alkyl electrophiles. This method allows access to primary, secondary, and tertiary boronic esters from the parent chlorides, which were previously inaccessible as coupling partners. The reaction proceeds in high yield with as little as 1000 ppm catalyst loading, while 5 mol % can provide high yields in as little as 30 min. Finally, radical-clock experiments revealed that at 0 °C direct borylation outcompetes alternative radical processes, thereby providing synthetically useful, temperature-controlled reaction outcomes.

Copper(I)-catalyzed borylative exo -cyclization of alkenyl halides containing unactivated double bond

A borylative exo-cyclization of alkenyl halides has been reported. The reaction includes the regioselective addition of a borylcopper(I) intermediate to unactivated terminal alkenes, followed by the intramolecular substitution of the resulting alkylcopper(I) moiety for the halide leaving groups. Experimental and theoretical investigations of the reaction mechanism have also been described. This reaction provides a new method for the synthesis of alkylboronates containing strained cycloalkyl structures from simple starting materials.

Homoallylboration and homocrotylboration of aldehydes

A simple method for addition of homoallylic fragments to aldehydes is described. Cyclopropanated allylboration reagents react with aldehydes in the presence of PhBCl2 to give high yields of bishomoallyl alcohols. Cyclopropanated cis-and trans-crotyl reage