351-78-0

Upstream product

• 359-19-3 1,1-dibromo-2,2-difluoroethane 
• 344865-12-9 di-isopropyl α-fluoro-β-hydroxyphenethylphosphonate 
• 100-52-7 benzaldehyde 
• 96385-23-8 P-(monofluoromethyl)triphenylphosphonium tetrafluoroborate 
• 591-50-4 iodobenzene 
• 68-12-2 N,N-dimethyl-formamide 
• 18001-47-3 styryltrimethylsilane 
• 118559-15-2 (E)-β-bromo-β-fluorostyrene 
• 201230-82-2 carbon monoxide 
• 71-36-3 butan-1-ol 
• 5396-91-8 1,5-diphenyl-3-pentanone 
• 83947-56-2 4,4,5,5-tetramethyl-2-((E)-styryl)-[1,3,2]dioxaborolane 
• 350-90-3 (Z/E)-2-fluoro-3-phenylprop-2-enoic acid 
• 2498-46-6 2-phenylacetamidine hydrochloride 

Downstream Products

• 1817-51-2 1-phenyl-1-hexyn-3-ol 
• 748785-01-5 N-[(5-trifluoromethyl)biphenyl-2-yl]benzamide 
• 1215017-02-9 C₂₀H₁₇F₂NO₄S₂ 
• 917381-61-4 5-(trifluoromethyl)-[1,1′-biphenyl]-2-amine 
• 637-50-3 1-phenylpropene 
• 122-78-1 phenylacetaldehyde 

Relevant academic research and scientific papers

Olefination via Cu-Mediated Dehydroacylation of Unstrained Ketones

The dehydroacylation of ketones to olefins is realized under mild conditions, which exhibits a unique reaction pathway involving aromatization-driven C-C cleavage to remove the acyl moiety, followed by Cu-mediated oxidative elimination to form an alkene between the α and β carbons. The newly adopted N′-methylpicolinohydrazonamide (MPHA) reagent is key to enable efficient cleavage of ketone C-C bonds at room temperature. Diverse alkyl- and aryl-substituted olefins, dienes, and special alkenes are generated with broad functional group tolerance. Strategic applications of this method are also demonstrated.

Terminal Alkenes from Acrylic Acid Derivatives via Non-Oxidative Enzymatic Decarboxylation by Ferulic Acid Decarboxylases

Fungal ferulic acid decarboxylases (FDCs) belong to the UbiD-family of enzymes and catalyse the reversible (de)carboxylation of cinnamic acid derivatives through the use of a prenylated flavin cofactor. The latter is synthesised by the flavin prenyltransferase UbiX. Herein, we demonstrate the applicability of FDC/UbiX expressing cells for both isolated enzyme and whole-cell biocatalysis. FDCs exhibit high activity with total turnover numbers (TTN) of up to 55000 and turnover frequency (TOF) of up to 370 min?1. Co-solvent compatibility studies revealed FDC's tolerance to some organic solvents up 20 % v/v. Using the in-vitro (de)carboxylase activity of holo-FDC as well as whole-cell biocatalysts, we performed a substrate profiling study of three FDCs, providing insights into structural determinants of activity. FDCs display broad substrate tolerance towards a wide range of acrylic acid derivatives bearing (hetero)cyclic or olefinic substituents at C3 affording conversions of up to >99 %. The synthetic utility of FDCs was demonstrated by a preparative-scale decarboxylation.

FLUORINATION METHOD

The present invention relates to a process for producing an organic compound comprising an 18F atom. The compounds comprising an 18F can be useful as PET ligands for use in diagnostics and/or scanning. The process of the invention comprises treating an organoboron compound, which organoboron compound comprises a boron atom bonded to an sp2 hybridised carbon atom, with (i) 18F – and (ii) a copper compound. The invention also provides the use of an organoboron compound, which organoboron compound comprises a boron atom bonded to an sp2 hybridised carbon atom, in a process for producing an organic compound comprising an 18F atom, which process comprises treating the organoboron compound with (i) 18F – and (ii) a copper compound. The invention also provides a compound of formula (XXXVII): wherein: each PGA is independently H or an alcohol protecting group; PGB is H or a carboxylic acid protecting group; each PGC is independently an amine protecting group; Z is a group selected from a boronic ester group, a boronic acid group, a borate group, and a trifluoroborate group; and a is an integer from 0 to 4.

New cofactor supports α,β-unsaturated acid decarboxylation via 1,3-dipolar cycloaddition

The bacterial ubiD and ubiX or the homologous fungal fdc1 and pad1 genes have been implicated in the non-oxidative reversible decarboxylation of aromatic substrates, and play a pivotal role in bacterial ubiquinone (also known as coenzyme Q) biosynthesis or microbial biodegradation of aromatic compounds, respectively. Despite biochemical studies on individual gene products, the composition and cofactor requirement of the enzyme responsible for in vivo decarboxylase activity remained unclear. Here we show that Fdc1 is solely responsible for the reversible decarboxylase activity, and that it requires a new type of cofactor: a prenylated flavin synthesized by the associated UbiX/Pad1. Atomic resolution crystal structures reveal that two distinct isomers of the oxidized cofactor can be observed, an isoalloxazine N5-iminium adduct and a N5 secondary ketimine species with markedly altered ring structure, both having azomethine ylide character. Substrate binding positions the dipolarophile enoic acid group directly above the azomethine ylide group. The structure of a covalent inhibitor-cofactor adduct suggests that 1,3-dipolar cycloaddition chemistry supports reversible decarboxylation in these enzymes. Although 1,3-dipolar cycloaddition is commonly used in organic chemistry, we propose that this presents the first example, to our knowledge, of an enzymatic 1,3-dipolar cycloaddition reaction. Our model for Fdc1/UbiD catalysis offers new routes in alkene hydrocarbon production or aryl (de)carboxylation.

FLUORINATION OF ORGANIC COMPOUNDS

Methods for fluorinating organic compounds are described herein.

Stereospecific preparation of symmetrical (1Z, 3Z)- and (1E, 3E)-2,3-difluoro-1,4-disubstituted-buta-1,3-dienes from 1-bromo-1-fluoroalkenes

A straightforward method to prepare symmetrical (1Z, 3Z)- and (1E, 3E)-2,3-difluoro-1,4-disubstituted-buta-1,3-dienes is described. High E/Z ratio 1-bromo-1-fluoroalkenes, prepared by isomerization from the E/Z ≈ 1:1 isomeric mixtures, reacted with Busub

Highly stereoselective synthesis of (E)- and (Z)-α-fluoro-α, β-unsaturated esters and (E)- and (Z)-α-fluoro-α,β- unsaturated amides from 1-bromo-1-fluoroalkenes via palladium-catalyzed carbonylation reactions

The highly stereoselective synthesis of (E)- and (Z)-α-fluoro- α,β-unsaturated esters and (E)- and (Z)-α-fluoro-α, β-unsaturated amides is described. 1-Bromo-1-fluoroalkenes (E/Z ≈ 1:1), which are readily available starting materials, have been found to i

Kinetic separation methodology for the stereoselective synthesis of (E)- and (Z)-alpha-fluoro-alpha,beta-unsaturated esters via the palladium-catalyzed carboalkoxylation of 1-bromo-1-fluoroalkenes.

[reaction: see text] Methodology for the stereoselective preparation of both (E)- and (Z)-alpha-fluoro-alpha,beta-unsaturated esters is described. 1-Bromo-1-fluoroalkenes (E/Z approximate 1:1) can be isomerized to high E/Z ratio mixtures, which participat

Fluorodesilylation of alkenyltrimethylsilanes: A new route to fluoroalkenes and difluoromethyl-substituted amides, alcohols or ethers

A range of alkenyltrimethylsilanes are converted to alkenyl fluorides by reaction with one equivalent of Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)), or difluoromethyl-substituted alcohols, ethers or amides using an excess of Selectfluor in the presence of various nucleophiles.

The simultaneous in-situ generation of aldehydes and phosphorus ylides: A convenient multi-step one-pot olefination protocol

The lithium α-(dimethylamino)alkoxides resulting from the nucleophilic addition of an organolithium reagent to N,N-dimethylformamide are basic enough to deprotonate alkyltriphenylphosphonium salts suspended in tetrahydrofuran. The aldehydes liberated by t