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Usage

Uses

Used in Organic Synthesis:
4-(TRIFLUOROMETHOXY)BENZYLBORONIC ACID & is utilized as a key building block in organic synthesis for its ability to form carbon-carbon and carbon-heteroatom bonds. This property is crucial for the creation of complex organic molecules and contributes to the advancement of chemical libraries.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 4-(TRIFLUOROMETHOXY)BENZYLBORONIC ACID & serves as a valuable intermediate in the development of new drugs. Its unique reactivity allows for the synthesis of a variety of bioactive compounds, potentially leading to the discovery of novel therapeutic agents.
Used in Agrochemical Development:
4-(TRIFLUOROMETHOXY)BENZYLBORONIC ACID & is also employed in the agrochemical sector, where it is used as a precursor in the synthesis of new pesticides and other crop protection agents. Its role in creating effective and environmentally friendly agrochemicals is of significant importance for sustainable agriculture.
Each application underscores the compound's versatility and the potential for further exploration in various chemical and biological fields.

InChI:InChI=1/C14H18BF3O3/c1-12(2)13(3,4)21-15(20-12)9-10-5-7-11(8-6-10)19-14(16,17)18/h5-8H,9H2,1-4H3

Upstream product

• 50824-05-0 4-trifluoromethoxybenzyl bromide 
• 73183-34-3 bis(pinacol)diborane 
• 78782-17-9 4,4,5,5-tetramethyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-1,3,2-dioxaborolane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 659-28-9 p-trifluoromethoxybenzaldehyde 
• 745783-97-5 triethyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane 
• 706-27-4 p-methyl-α,α,α-trifluoromethoxybenzene 

Downstream Products

• 719277-21-1 N-(4-(trifluoromethoxy)benzyl)acetamide 
• 1201331-15-8 potassium (4-(trifluoromethoxy)benzyl)trifluoroborate 
• 1361005-24-4 C₂₄H₁₈F₃NO₂ 
• 1457967-22-4 N⁴-benzyl-3-nitro-6-(4-(trifluoromethoxy)benzyl)-N²-(2,4,4-trimethylpentan-2-yl)pyridine-2,4-diamine 

Relevant academic research and scientific papers

Metal-Free Direct Deoxygenative Borylation of Aldehydes and Ketones

Direct conversion of aldehydes and ketones into alkylboronic esters via deoxygenative borylation represents an unknown yet highly desirable transformation. Herein, we present a one-step and metal-free method for carbonyl deoxy-borylation under mild conditions. A wide range of aromatic aldehydes and ketones are tolerated and successfully converted into the corresponding benzylboronates. By the same deoxygenation manifold with aliphatic aldehydes and ketones, we also enable a concise synthesis of 1,1,2-tris(boronates), a family of compounds that currently lack efficient synthetic methods. Given its simplicity and versatility, we expect that this novel borylation approach could show great promise in organoboron synthesis and inspire more carbonyl deoxygenative transformations in both academic and industrial settings.

Regioselective α-benzylation of 3-iodoazetidine via Suzuki cross-coupling

An efficient protocol for the synthesis of α-benzyl azetidines starting from benzylboronic acid pinacol ester derivatives and 3-iodoazetidine was developed. A wide range of α-benzyl azetidine derivatives were obtained in moderate to good yields with high regioselectivity (>99%).

Pd-catalyzed cross-coupling of 1,1-diborylalkanes with aryl triflates

The Pd-catalyzed synthesis of benzylboronic esters through coupling of aryl triflates with 1,1-diborylalkane under ambient conditions is described. Varieties of primary and secondary arylboronic esters could be successfully synthesized by this strategy. C

Iridium-Catalyzed Borylation of Primary Benzylic C-H Bonds without a Directing Group: Scope, Mechanism, and Origins of Selectivity

Primary benzylic boronate esters are useful intermediates in organic synthesis, but these reagents cannot be prepared by hydroboration. The benzylic C-H borylation of methylarenes would be a method to form these products, but such reactions without neat methylarene or a directing group are unknown. We report an approach to divert the borylation of methylarenes from aromatic positions to benzylic positions with a silylborane as reagent and a new iridium catalyst containing an electron-deficient phenanthroline as ligand. This system forms benzylic boronate esters selectively over the corresponding aryl boronate esters. An Ir diboryl monosilyl complex ligated by the phenanthroline was isolated and determined to be the resting state of the catalyst. Mechanistic studies show that this complex is kinetically competent to be an intermediate in the catalytic process. Kinetic studies of benzylic and aryl C-H borylation catalyzed by various Ir complexes show that the rate of aryl C-H borylation decreases with decreasing electron density at the metal center of the Ir catalyst, but that the rate of benzylic C-H borylation is less sensitive to the degree of electron density at the metal center of the Ir catalyst. Kinetic and computational studies suggest that the two borylation reactions respond differently to the degree of electron density at the metal center because they occur with different turnover-limiting steps. The turnover-limiting step in the borylation of aryl C-H bonds is known to be C-H oxidative addition, but the turnover-limiting step of the borylation of benzylic C-H bonds appears to be an isomerization prior to C-B reductive elimination.

Iron-catalyzed borylation of alkyl, allyl, and aryl halides: Isolation of an iron(I) boryl complex

Activation of B2pin2 with tBuLi facilitates the Fe-catalyzed borylation of alkyl, allyl, benzyl, and aryl halides via the formation of Li[B2pin2(tBu)] (1). The reaction of 1 with a representative iron phosphine precatalyst generates the unique iron(I) boryl complex [Fe(Bpin)(dpbz)2] (2).