1359844-10-2

Upstream product

• 398-23-2 4,4'-difluorobiphenyl 
• 73183-34-3 bis(pinacol)diborane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 140369-67-1 (4'-fluoro-[1,1'-biphenyl]-4-yl)boronic acid 
• 586-77-6 4-bromo-N,N-dimethylaniline 
• 117530-21-9 4′-fluoro-N,N-dimethyl-[1,1′-biphenyl]-4-amine 
• 17865-11-1 (4-(trimethylsilyl)phenyl)boronic acid 
• 1186026-67-4 1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trimethylsilyl)benzene 
• 459-45-0 4-fluorobenzenediazonium tetrafluoroborate 
• 398-22-1 4-chloro-4′-fluoro-1,1′-biphenyl 
• 5731-10-2 4'-fluoro-biphenyl-4-carboxylic acid 
• 782480-50-6 4′-fluoro-[1,1′-biphenyl]-4-carbonyl chloride 
• 1350618-09-5 S-ethyl 4'-fluoro-[1,1'-biphenyl]-4-carbothioate 
• 5798-76-5 phenyl 4-bromobenzoate 

Downstream Products

• 1367127-90-9 methyl 4-chloro-6-(4'-fluoro-[1,1'-biphenyl]-4-yl)picolinate 
• 1367127-88-5 methyl 6-chloro-4-(4'-fluoro-[1,1'-biphenyl]-4-yl)picolinate 
• 207611-87-8 4,4′-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1′-biphenyl 
• 1367125-90-3 (S)-4-(1,2-dihydroxyethyl)-6-(4'-fluoro-[1,1'-biphenyl]-4-yl)picolinamide 
• 1367127-94-3 6-(4'-fluoro-[1,1'-biphenyl]-4-yl)-4-vinylpicolinamide 
• 1367127-92-1 methyl 6-(4'-fluoro-[1,1'-biphenyl]-4-yl)-4-vinylpicolinate 

Relevant academic research and scientific papers

LiHMDS-Promoted Palladium or Iron-Catalyzed ipso-Defluoroborylation of Aryl Fluorides

A novel and efficient method for the synthesis of arylboronic acid pinacol esters via a palladium- or iron-catalyzed cross-coupling reaction of aryl fluorides with bis(pinacolato)diboron (B2pin2) in the presence of LiHMDS was developed. The Pd-catalyzed defluoroborylation of fluoroarenes is compatible with a variety of functional groups such as primary and secondary amine, ketone, trifluoromethyl, alkoxy, and boryl. Remarkably, no external ligand is required for enhanced conversion efficiency.

Cross-Coupling through Ag(I)/Ag(III) Redox Manifold

In ample variety of transformations, the presence of silver as an additive or co-catalyst is believed to be innocuous for the efficiency of the operating metal catalyst. Even though Ag additives are required often as coupling partners, oxidants or halide scavengers, its role as a catalytically competent species is widely neglected in cross-coupling reactions. Most likely, this is due to the erroneously assumed incapacity of Ag to undergo 2e? redox steps. Definite proof is herein provided for the required elementary steps to accomplish the oxidative trifluoromethylation of arenes through AgI/AgIII redox catalysis (i. e. CEL coupling), namely: i) easy AgI/AgIII 2e? oxidation mediated by air; ii) bpy/phen ligation to AgIII; iii) boron-to-AgIII aryl transfer; and iv) ulterior reductive elimination of benzotrifluorides from an [aryl-AgIII-CF3] fragment. More precisely, an ultimate entry and full characterization of organosilver(III) compounds [K]+[AgIII(CF3)4]? (K-1), [(bpy)AgIII(CF3)3] (2) and [(phen)AgIII(CF3)3] (3), is described. The utility of 3 in cross-coupling has been showcased unambiguously, and a large variety of arylboron compounds was trifluoromethylated via [AgIII(aryl)(CF3)3]? intermediates. This work breaks with old stereotypes and misconceptions regarding the inability of Ag to undergo cross-coupling by itself.

Photoinduced Deaminative Borylation of Unreactive Aromatic Amines Enhanced by CO2

Herein, direct unreactive C-N borylation of aromatic amines by a photocatalyst was achieved. The C-N borylation of aromatic amines with bis(pinacolato)diboron (B2pin2) proceeded using a pyrene catalyst under light irradiation to afford desired borylated products and aminoborane as a byproduct. The yield of the borylated product improved under a CO2 atmosphere which probably reduced the inhibitory effect of aminoborane. Mechanistic studies suggested that the C-N bond cleavage and C-B bond formation proceeded via a concerted pathway.

Iron-Catalyzed Borylation of Aryl Ethers via Cleavage of C-O Bonds

Herein, we report the iron-catalyzed borylation of aryl ethers and aryl amines via cleavage of C-O and C-N bonds. This protocol does not require the use of Grignard reagents and displays a broad substrate scope, which allows the late-stage borylation. It also provides facile access to multisubstituted arenes through C-H functionalization using 2-pyridyloxy as the directing group.

Nickel-catalysed decarbonylative borylation of aroyl fluorides

The first Ni(cod)2/PPh3 catalyst system has been established for decarbonylative borylation of aroyl fluorides with bis(pinacolato)diboron. A wide range of functional groups in the substrates were well tolerated. The ease of access of the starting aroyl fluorides indicates that these results might become an alternative to the existing decarbonylation events.

Light-Induced Gold-Catalyzed Hiyama Arylation: A Coupling Access to Biarylboronates

Organoboron compounds are versatile synthetic building blocks. We herein report a new strategy, a photochemical gold-catalyzed chemo-selective Hiyama arylation of B,Si bifunctionalized reagents with diazonium salts, which is orthogonal to common strategies and therefore a unique tool for synthesis of valuable biarylboronates. With this new methodology a wide array of diversely functionalized sp2- and sp3-hybridized biarylboronates were obtained. Notably, the synergism of gold catalysis with copper catalysis or palladium catalysis, allows for one-pot iterative C?X (heteroatom) and C?C couplings for the rapid assembly of several simple fragments to relatively complex molecules. Mechanistic studies indicated that photosensitizer-free conditions were superior to gold/Ru(bpy)3Cl2 dual catalysis.

Rhodium-Catalyzed Decarbonylative Borylation of Aromatic Thioesters for Facile Diversification of Aromatic Carboxylic Acids

Transformation of aromatic thioesters into arylboronic esters was achieved efficiently using a rhodium catalyst. The broad functional-group tolerance and mild conditions of the method have allowed for the two-step decarboxylative borylation of a wide range of aromatic carboxylic acids, including commercially available drugs.

Iron-Catalyzed Borylation of Aryl Chlorides in the Presence of Potassium t-Butoxide

A catalytic amount of an inorganic iron salt such as Fe(acac)3 catalyzes borylation of various aryl and heteroaryl chlorides with bis(pinacolato)diboron, where the presence of potassium t-butoxide is crucially important. The alkoxide is considered to produce in situ an electron-rich iron alkoxide complex as the active species. The reaction requires only an iron salt and potassium t-butoxide as promoters and is easily scalable. The arylboron compound prepared by this reaction can be further coupled in situ with an aryl halide under the Suzuki-Miyaura conditions.

Functional Group Interconversion: Decarbonylative Borylation of Esters for the Synthesis of Organoboronates

A new and efficient nickel-catalyzed decarbonylative borylation reaction of carboxylic acid esters with bis(pinacolato)-diboron has been developed. This transformation allows access to structurally diverse aryl as well as alkenyl and alkyl boronate esters with high reactivity, broad substrate scope, and excellent functional-group tolerance. Further experiments show that this protocol can be carried out on a gram scale and applied to orthogonal synthetic strategies.

Design and synthesis of boronic acid inhibitors of endothelial lipase

Endothelial lipase (EL) and lipoprotein lipase (LPL) are homologous lipases that act on plasma lipoproteins. EL is predominantly a phospholipase and appears to be a key regulator of plasma HDL-C. LPL is mainly a triglyceride lipase regulating (V)LDL levels. The existing biological data indicate that inhibitors selective for EL over LPL should have anti-atherogenic activity, mainly through increasing plasma HDL-C levels. We report here the synthesis of alkyl, aryl, or acyl-substituted phenylboronic acids that inhibit EL. Many of the inhibitors evaluated proved to be nearly equally potent against both EL and LPL, but several exhibited moderate to good selectivity for EL.