704-36-9

Usage

InChI:InChI=1/C9H8F2O/c1-6-2-4-7(5-3-6)8(12)9(10)11/h2-5,9H,1H3

Upstream product

• 686-11-3 N,N-diethyl-2,2-difluoroacetamide 
• 2417-95-0 p-tolyllithium 
• 413597-89-4 ((2,2-difluoro-1-(p-tolyl)vinyl)oxy)trimethylsilane 
• 394-59-2 2,2,2-trifluoro-1-(p-tolyl)ethanone 
• 1337572-01-6 C₁₈H₂₂F₂O₂SSi 
• 50562-10-2 2,2-difluoro-1-(4-methylphenyl)ethanol 
• 104-87-0 4-methyl-benzaldehyde 
• 142492-01-1 2,2-difluoro-N-methoxy-N-methylacetamide 
• 106-38-7 para-bromotoluene 
• 13422-78-1 3-oxo-3-p-toluoylpropanoic acid 
• 720-94-5 4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione 
• 122-00-9 para-methylacetophenone 
• 454-31-9 ethyl difluoroacetate 
• 1044589-10-7 (2,2-difluoro-1-p-tolyl-ethylidene)(4-fluoro-phenyl)amine 

Downstream Products

• 50562-10-2 2,2-difluoro-1-(4-methylphenyl)ethanol 
• 50562-11-3 Toluene-4-sulfonic acid 2,2-difluoro-1-p-tolyl-ethyl ester 
• 50561-97-2 1-(2,2-difluoroethyl)-4-methylbenzene 
• 1577233-03-4 2,2-difluoro-2-(4-methoxyphenyl)-1-(p-tolyl)ethanone 
• 704-33-6 1-(3,3-difluoroprop-1-en-2-yl)-4-methylbenzene 
• 69843-09-0 1-methyl-4-(3,3,3-trifluoroprop-1-en-2-yl)benzene 

Relevant academic research and scientific papers

A Carbene Strategy for Progressive (Deutero)Hydrodefluorination of Fluoroalkyl Ketones

Hydrodefluorination is one of the most promising chemical strategies to degrade perfluorochemicals into partially fluorinated compounds. However, controlled progressive hydrodefluorination remains a significant challenge, owing to the decrease in the stre

Transaminases as suitable catalysts for the synthesis of enantiopure β,β-difluoroamines

Transaminases have shown the ability to catalyze the amination of a series of aliphatic and (hetero)aromatic α,α-difluorinated ketones with high stereoselectivity, thus providing the corresponding β,β-difluoroamines in high isolated yields (55–82%) and ex

Biocatalytic Strategy for the Highly Stereoselective Synthesis of CHF2-Containing Trisubstituted Cyclopropanes

The difluoromethyl (CHF2) group has attracted significant attention in drug discovery and development efforts, owing to its ability to serve as fluorinated bioisostere of methyl, hydroxyl, and thiol groups. Herein, we report an efficient biocat

Direct electrochemical hydrodefluorination of trifluoromethylketones enabled by non-protic conditions

CF2H groups are unique due to the combination of their lipophilic and hydrogen bonding properties. The strength of H-bonding is determined by the group to which it is appended. Several functional groups have been explored in this context includ

Visible light-promoted umpolung coupling of aryl tri-/difluoroethanones with 2-alkenylpyridines

Tertiary alcohols bearing a trifluoromethyl group are of considerable medicinal interest. Using an umpolung strategy, we herein report the first intermolecular reductive cross-coupling of aryl tri-/difluoroethanones with 2-alkenylpyridines with the aid of a Br?nsted acid catalyst upon visible-light irradiation. This metal-free reaction is operationally simple and performed at ambient temperature, allowing access to desired tertiary alcohols with tri-/difluoromethyl groups in moderate to excellent yields. The commercially available and easily handled Hantzsch ester effectively serves as an electron donor, as well as a hydrogen atom source.

Catalytic Enantioselective Synthesis of Highly Functionalized Difluoromethylated Cyclopropanes

The first catalytic asymmetric synthesis of highly functionalized difluoromethylated cyclopropanes is described. The method, based on a rhodium-catalyzed cyclopropanation of difluoromethylated olefins, gives access to a broad range of cyclopropanes bearing ester, ketone, or nitro functional groups. By using Rh2((S)-BTPCP)4 as a catalyst, the corresponding products were obtained in high yields and high diastereo- and enantioselectivities (up 20:1 d.r. and 99 % ee). This methodology allowed preparation of enantioenriched difluoromethylcyclopropanes for the first time.

Photoredox Generation of Carbon-Centered Radicals Enables the Construction of 1,1-Difluoroalkene Carbonyl Mimics

Described is a facile, scalable route to access functional-group-rich gem-difluoroalkenes. Using visible-light-activated catalysts in conjunction with an arsenal of carbon-radical precursors, an array of trifluoromethyl-substituted alkenes undergoes radical defluorinative alkylation. Nonstabilized primary, secondary, and tertiary radicals can be used to install functional groups in a convergent manner, which would otherwise be challenging by two-electron pathways. The process readily extends to other perfluoroalkyl-substituted alkenes. In addition, we report the development of an organotrifluoroborate reagent to expedite the synthesis of the requisite trifluoromethyl-substituted alkene starting materials.

Practical Access to Difluoromethyl Ketones via Straightforward Decarboxylative Difluorination of β-Ketoacids

A facile synthetic approach to a series of difluoromethyl ketones from β-ketoacids has been described. This transformation is achieved through the straightforward decarboxylative difluorination of β-ketoacids in the absence of any catalyst. Furthermore, the resulted difluoromethyl ketones can be easily converted into corresponding difluoromethylated building blocks for pharmaceuticals and materials. (Figure presented.).

One-pot synthesis of difluoromethyl ketones by a difluorination/fragmentation process

Difluoromethyl ketones are an under-studied class of ketones which have great potential as useful building blocks for materials and drug design. Here we report a simple and convenient synthesis of this class of compounds via a one-pot difluorination/fragm

Improvements and Applications of the Transition Metal-Free Asymmetric Allylic Alkylation using Grignard Reagents and Magnesium Alanates

Two new N-heterocyclic carbene (NHC) ligands have been synthesized and employed in the transition metal-free asymmetric allylic alkylation (AAA) mediated by Grignard reagents and magnesium alanates. The employment of these ligands showed high yields and improved regio- and enantioselectivity in the formation of tertiary and quaternary stereocenters. Moreover, the low catalyst loading (up to 0.3 mol%) and high scalability (up to 10 mmol) of this improved methodology provide a convenient access to biologically active compounds and synthetically valuable intermediates.