36329-86-9

Usage

Uses

Used in Pharmaceutical Research:
(4-Phenylbutyl)boronic acid is used as a key intermediate in the synthesis of various pharmaceutical compounds due to its ability to form stable complexes with diol-containing molecules. This property aids in the development of new drugs with improved efficacy and selectivity.
Used in Organic Synthesis:
In the field of organic synthesis, (4-Phenylbutyl)boronic acid is utilized as a versatile building block for the creation of a wide range of organic molecules. Its unique structure allows for the formation of carbon-carbon bonds and the synthesis of complex organic compounds.
Used in Suzuki-Miyaura Cross-Coupling Reactions:
(4-Phenylbutyl)boronic acid is employed as a popular reagent in Suzuki-Miyaura cross-coupling reactions, a powerful method for forming carbon-carbon bonds in organic chemistry. This application is particularly relevant in the synthesis of complex organic molecules and the development of novel materials.
Used in Material Science:
In material science, (4-Phenylbutyl)boronic acid is used as a component in the development of new materials with specific properties. Its ability to form stable complexes with diol-containing molecules makes it a valuable asset in the creation of materials with tailored characteristics for various applications.

Upstream product

• 768-56-9 4-Phenylbut-1-ene 
• 13633-25-5 1-Bromo-4-phenylbutane 
• 167693-07-4 4-phenyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butane 
• 14044-65-6 borane-THF 
• 27152-04-1 (4-phenylbutyl)magnesium bromide 

Downstream Products

• 476334-39-1 (1S,2S,6R,8S)-2,9,9-Trimethyl-4-(4-phenyl-butyl)-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]decane 
• 7726-45-6 5-phenylvaleronitrile 
• 123455-90-3 1,1-difluoro-6-phenyl-1-hexene 
• 476334-40-4 (1S,2S,6R,8S)-4-((S)-1-Chloro-5-phenyl-pentyl)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]decane 

Relevant academic research and scientific papers

Coupling of Trifluoroacetaldehyde N-Triftosylhydrazone with Organoboronic Acids for the Synthesis of gem-Difluoroalkenes

The synthesis of alkyl gem-difluoroalkenes remains a difficult task in organic synthesis. Here, we report a general and efficient approach for tackling this problem by gem-difluoroolefination of trifluoroacetaldehyde N-triftosylhydrazone with organoboronic acids. This protocol is operationally simple, free of transition metals, and suitable for a broad range of organoboronic acids. Moreover, the utility of the products was demonstrated by further conversion of the gem-difluorovinyl group.

CU-AND NI-CATALYZED DECARBOXYLATIVE BORYLATION REACTIONS

The invention is directed to methods of converting a carboxylic acid group in a compound, via a redox active ester, to a corresponding boronic ester by treatment with bis(pinacolato)diboron-alkyllithium complex in the presence of a ligand, a Ni(ll) salt or a copper salt, and an Mg(ll) salt, in the presence of an alkyllithium or a lithium hydroxide or alkoxide salt. The product pinacolato boronate ester can be cleaved to provide a boronic acid. The invention is also directed to methods of preparing various compounds of medical value comprising boronic acid groups, and to novel boronic-acid containing compounds of medicinal value, including an atorvastatin boronic acid analog, a vancomycin aglycone boronic acid analog, and boronic acid containing elastase inhibitors mCBK319, mCBK320, mCBK323, and RPX-7009.

Decarboxylative borylation

The widespread use of alkyl boronic acids and esters is frequently hampered by the challenges associated with their preparation.We describe a simple and practical method to rapidly access densely functionalized alkyl boronate esters from abundant carboxylic substituents. This broad-scope nickel-catalyzed reaction uses the same activating principle as amide bond formation to replace a carboxylic acid moiety with a boronate ester. Application to peptides allowed expedient preparations of a-amino boronic acids, often with high stereoselectivity, thereby facilitating synthesis of the alkyl boronic acid drugs Velcade and Ninlaro as well as a boronic acid version of the iconic antibiotic vancomycin. The reaction also enabled the discovery and extensive biological characterization of potent human neutrophil elastase inhibitors, which offer reversible covalent binding properties.

Amino acid-promoted C-H alkylation with alkylboronic acids using a removable directing group

Palladium-catalyzed C-H alkylation reaction with alkylboronic acids has successfully been developed using a removable pyridyldiisopropylsilyl directing group. The amino acid played a crucial role as a ligand in the reaction. The alkylation protocol is also applicable to the coupling of C(sp3)-H bonds with alkylboronic acids.

Deboronative cyanation of potassium alkyltrifluoroborates: Via photoredox catalysis

A photoredox catalytic method was developed for the direct cyanation of alkyltrifluoroborates. This reaction provides a new and useful transformation of the easily available alkyltrifluoroborates. The photocatalytic reaction can tolerate a variety of functional groups with mild reaction conditions. Mechanistic investigations are consistent with the present reaction following a radical pathway.

P1 Phenethyl peptide boronic acid inhibitors of HCV NS3 protease

A series of peptide boronic acids containing extended, hydrophobic P1 residues was prepared to probe the shallow, hydrophobic S1 region of HCV NS3 protease. The p-trifluoromethylphenethyl P1 substituent was identified as optimal with respect to inhibitor potency for NS3 and selectivity against elastase and chymotrypsin.