128796-45-2

Basic information

• Product Name: Boroxin, tris[4-(trifluoromethyl)phenyl]-
• CAS NO: 128796-45-2
• Molecular Formula: C21H12B3F9O3
• Molecular Weight: 515.743
• Mol File: 128796-45-2.mol

Chemical Properties

• CAS DataBase Reference: Boroxin, tris[4-(trifluoromethyl)phenyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Boroxin, tris[4-(trifluoromethyl)phenyl]-(128796-45-2)
• EPA Substance Registry System: Boroxin, tris[4-(trifluoromethyl)phenyl]-(128796-45-2)

Safety Data

• Hazardous Substances Data: 128796-45-2(Hazardous Substances Data)

Upstream product

• 150-46-9 triethyl borate 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 128796-39-4 4-trifluoromethylphenylboronic acid 

Downstream Products

• 113845-69-5 4-(4-trifluoromethylphenyl)morpholine 
• 1424035-30-2 (S)-2-(1-(4-(trifluoromethyl)phenyl)ethyl)naphthalene 
• 1424035-46-0 (R)-2-(1-(4-(trifluoromethyl)phenyl)propyl)naphthalene 
• 1426442-26-3 (R)-2-(phenyl(4-(trifluoromethyl)phenyl)methyl)naphthalene 
• 1424035-53-9 (S)-2-(phenyl(4-(trifluoromethyl)phenyl)methyl)naphthalene 
• 1334287-96-5 (S)-4-methoxy-N-(2,2,2-trifluoro-1-(4-(trifluoromethyl)phenyl)ethyl)aniline 
• 345-88-0 1-phenyl-1-(4-trifluoromethylphenyl)ethylene 
• 1380243-09-3 2,3-diphenyl-5-(trifluoromethyl)-1H-inden-1-one 
• 1198576-76-9 1-benzyl-5-(trifluoromethyl)-1,2,3-triphenyl-1H-indene 
• 6565-03-3 (1-(4-(trifluoromethyl)phenyl)ethene-1,2-diyl)dibenzene 
• 1017280-77-1 C₂₈H₂₂F₃NO₄ 
• 98-08-8 α,α,α-trifluorotoluene 
• 402-44-8 4-Fluorobenzotrifluoride 

Relevant articles and documents

Rhodium-Catalyzed Asymmetric Arylation/Defluorination of 1-(Trifluoromethyl)alkenes Forming Enantioenriched 1,1-Difluoroalkenes

The reaction of 1-(trifluoromethyl)alkenes (CF3CH=CHR) with arylboroxines (ArBO)3 in the presence of a chiral diene-rhodium catalyst gave high yields of chiral 1,1-difluoroalkenes (CF2=CHC?HArR) with high enantioselectivity (≥95% ee). The reaction is assumed to proceed through β-fluoride elimination of a β,β,β-trifluoroalkylrhodium intermediate that is generated by arylrhodation of the 1-(trifluoromethyl)alkene.

Nickel(II)-Catalyzed Addition of Aryl and Heteroaryl Boroxines to the Sulfinylamine Reagent TrNSO: The Catalytic Synthesis of Sulfinamides, Sulfonimidamides, and Primary Sulfonamides

We report a redox-neutral Ni(II)-catalyzed addition of (hetero)aryl boroxines to N-sulfinyltritylamine (TrNSO). The reactions use a catalyst generated from the combination of commercial, air-stable NiCl2·(glyme) and a commercially available bipyridine lig

Copper-Catalyzed Asymmetric Arylation of N-Heteroaryl Aldimines: Elementary Step of a 1,4-Insertion

Copper complexes of monodentate phosphoramidites efficiently promote asymmetric arylation of N-azaaryl aldimines with arylboroxines. DFT calculations and experiments support an elementary step of 1,4-insertion in the reaction pathway, a step in which an aryl-copper species adds directly across four atoms of C=N?C=N in the N-azaaryl aldimines.

Kinetics and Mechanism of the Palladium-Catalyzed Oxidative Arylating Carbocyclization of Allenynes

Pd-catalyzed C-C bond-forming reactions under oxidative conditions constitute a class of important and widely used synthetic protocols. This Article describes a mechanistic investigation of the arylating carbocyclization of allenynes using boronic acids and focuses on the correlation between reaction conditions and product selectivity. Isotope effects confirm that either allenic or propargylic C-H activation occurs directly after substrate binding. With an excess of H2O, a triene product is selectively formed via allenic C-H activation. The latter C-H activation was found to be turnover-limiting and the reaction zeroth order in reactants as well as the oxidant. A dominant feature is continuous catalyst activation, which was shown to occur even in the absence of substrate. Smaller amounts of H2O lead to mixtures of triene and vinylallene products, where the latter is formed via propargylic C-H activation. The formation of triene occurs only in the presence of ArB(OH)2. Vinylallene, on the other hand, was shown to be formed by consumption of (ArBO)3 as a first-order reactant. Conditions with sub-stoichiometric BF3·OEt2 gave selectively the vinylallene product, and the reaction is first order in PhB(OH)2. Both C-H activation and transmetalation influence the reaction rate. However, with electron-deficient ArB(OH)2, C-H activation is turnover-limiting. It was difficult to establish the order of transmetalation vs C-H activation with certainty, but the results suggest that BF3·OEt2 promotes an early transmetalation. The catalytically active species were found to be dependent on the reaction conditions, and H2O is a crucial parameter in the control of selectivity.

Unveiling the role of boroxines in metal-free carbon-carbon homologations using diazo compounds and boronic acids

By means of computational and experimental mechanistic studies the fundamental role of boroxines in the reaction between diazo compounds and boronic acids was elucidated. Consequently, a selective metal-free carbon-carbon homologation of aryl and vinyl boroxines using TMSCHN2, giving access to TMS-pinacol boronic ester products, was developed.

Palladium(II)-Catalyzed Enantioselective Synthesis of α-(Trifluoromethyl)arylmethylamines

We describe a method for the synthesis of α-(trifluoromethyl)arylmethylamines that consists of the palladium(II)-catalyzed addition of arylboroxines to imines derived from trifluoroacetaldehyde. Palladium acetate is used as a catalyst with electron-neutral or electron-rich arylboroxines, and it was found that addition of an ammonium or silver salt was crucial to promote the reaction of electron-poor boroxines. With (S)-t-Bu-PyOX as the chiral ligand, this method delivers a variety of α-trifluoromethylated amines in 57-91% yield and with greater than 92% ee in most cases.

Asymmetric Synthesis of Triarylmethanes by Rhodium-Catalyzed Enantioselective Arylation of Diarylmethylamines with Arylboroxines

The reaction of racemic diarylmethylamines, (Ar1Ar2CHNR2), where Ar1 is substituted with a 2-hydroxy group, with arylboroxines (Ar3BO)3 in the presence of a chiral diene-rhodium catalyst gave high yields of chiral triarylmethanes (Ar1Ar2CH?Ar3) with high enantioselectivity (up to 97% ee). The reaction is assumed to proceed through o-quinone methide intermediates which undergo Rh-catalyzed asymmetric 1,4-addition of the arylboron reagents.

Direct Amidation of N-Boc- and N-Cbz-Protected Amines via Rhodium-Catalyzed Coupling of Arylboroxines and Carbamates

N-Boc- and N-Cbz-protected amines are directly converted into amides by a novel rhodium-catalyzed coupling of arylboroxines and carbamates, replacing the traditional two-step deprotection-condensation sequence. Both protected anilines and aliphatic amines are efficiently transformed into a wide variety of secondary benzamides, including sterically hindered and electron-deficient amides, as well as in the presence of acid-labile and reducible functional groups.

Enantioselective, nickel-catalyzed suzuki cross-coupling of quinolinium ions

Quinolinium ions are engaged in an asymmetric, Ni-catalyzed Suzuki cross-coupling to yield 2-aryl- and 2-heteroaryl-1,2-dihydroquinolines. Key to the development of this method is the use of a Ni(II) precatalyst that activates without the need for strong reductants or high temperatures. The Ni-iminium activation mode is demonstrated as an exceptionally mild pathway to generate enantioenriched products from racemic starting materials.

Diastereoselective synthesis of vicinally bis(trifluoromethylated) alkylboron compounds through successive insertions of 2,2,2-trifluorodiazoethane

The usefulness of embedded CF3 substituents within organic substructures necessitates the development of diverse methods for incorporating this functional group. A recently reported route to α-trifluoromethylated alkylboron compounds by an α-transfer mechanism has now been extended to the synthesis of unprecedented, vicinally ditrifluoromethylated alkylboron compounds in a diastereoselective fashion. The utility of these products is highlighted by conversion of the C-B bond into other functional groups.