1184844-25-4

Upstream product

• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 264279-00-7 4,4,4-trifluoro-1-(4-methoxyphenyl)-2-butyn-1-ol 
• 3592-47-0 Benzaldehyde-d 
• 1269758-75-9 1-deuterio-4,4,4-trifluoro-1-phenylbut-2-yn-1-ol 
• 93-89-0 benzoic acid ethyl ester 
• 21175-64-4 1,1-dideuteriophenylmethanol 
• 60512-57-4 1-(2,2-dibromovinyl)-4-methoxybenzene 
• 89965-74-2 1,1,1-trifluoro-4-(4-methoxyphenyl)but-3-yn-2-one 
• 89619-11-4 4-(4-methoxyphenyl)-1,1,1-trifluorobut-3-yn-2-ol 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 1246025-14-8 (R)-4,4,4-trifluoro-3-(1H-indol-3-yl)-1-(4-methoxyphenyl)butan-1-one 
• 1453495-82-3 (3S,4S)-3-butyl-6-(4-methoxyphenyl)-4-(trifluoromethyl)-3,4-dihydro-2H-pyran-2-one 
• 1453496-06-4 C₂₀H₁₇F₃O₃ 
• 1453495-92-5 (3S,4S)-6-(4-methoxyphenyl)-3-methyl-4-(trifluoromethyl)-3,4-dihydro-2H-pyran-2-one 
• 1226965-56-5 4,4,4-trifluoro-1-(4-methoxyphenyl)-3-phenyl-1-butanone 
• 1226965-51-0 4,4,4-trifluoro-1-(4-methoxyphenyl)-2-phenyl-2-buten-1-one 

Relevant academic research and scientific papers

Rh-Catalyzed C-H alkylation enabling modular synthesis of CF3-substituted benzannulated macrocyclic inhibitors of B cell responses

Inspired by aspirin and chalcone, herein, we describe a modular biomimetic strategy to achieve a new class of CF3-bearing benzannulated macrolactams. The key to the success of macrolactams was the utilization of a highly chemoselective Rh(iii)-catalyzed native carboxylic acid-directed C-H alkylation. Moreover, the unique CF3-containing benzannulated macrocycles showed decent immunosuppressive effects on B cellsin vitro, including proliferation, activation, and antibody production upon specific stimulation implicating TLR and BCR signaling.

Rh(III)-Catalyzed [3 + 2] Annulation via C-H Activation: Direct Access to Trifluoromethyl-Substituted Indenamines and Aminoindanes

The rhodium(III)-catalyzed direct C-H addition and annulation of benzimidates and aldimines with β-(trifluoromethyl)-α,β-unsaturated ketones is described. This protocol provides the facile and efficient formation of various trifluoromethyl-containing inde

Lewis Acid-Catalyzed Rearrangement of Fluoroalkylated Propargylic Alcohols: An Alternative Approach to β-Fluoroalkyl-α,β-enones

A practical Lewis acid-catalyzed Meyer-Schuster rearrangement of fluoroalkylated propargylic alcohols, leading to a series of β-fluoroalkyl-α,β-enones, is developed. The methodology reported herein features moderate to high yields and high stereoselectivi

Gold-catalyzed synthesis of β-trifluoromethylated α,β-unsaturated ketones from CF3-substituted propargylic carboxylates and their reactivity in Diels-Alder reactions

The synthesis of fluorinated synthetic intermediates has become a field of intense research in organic chemistry. In this article, we report the application of a gold-catalyzed rearrangement to the synthesis of β-trifluoromethylated α,β-unsaturated ketone

Highly regio- and stereoselective hydrosilylation of β-fluoroalkylated α,β-unsaturated ketones

Treatment of β-fluoroalkylated α,β-unsaturated ketones with 10.2 equiv of triethylsilane in the presence of 3 mol% of Co2(CO)8 in dichloroethane at the reflux temperature for 4 h gave 1,4-hydrosilylated adducts in a highly regio- and

Stereospecific asymmetric N-heterocyclic carbene (NHC)-catalyzed redox synthesis of trifluoromethyl dihydropyranones and mechanistic insights

N-Heterocyclic carbene (NHC)-catalyzed redox asymmetric hetero-Diels-Alder reactions of α-aroyloxyaldehydes with β-trifluoromethyl enones generates synthetically useful dihydropyranones containing a stereogenic trifluoromethyl substituent in good yields (up to 81%) and excellent diastereoselectivity and enantioselectivity (up to >95:5 dr and >99% ee). The process is stereospecific, with use of either (E)- or (Z)-β- trifluoromethyl enones forming syn- or anti-dihydropyranone products, respectively. Mechanistic studies through in situ kinetic analysis of the reaction reveal key differences in reactivity between chiral NHC precursor 1 and an achiral NHC precursor.

Application of Mitsunobu reagents to redox Isomerization of CF 3-containing propargylic alcohols to (E)-α,β-enones

Isomerization of CF3-containing secondary propargylic alcohols proceeds with excellent E selectivity by treatment with Mitsunobu reagents, tris- (p-methoxyphenyl)phosphine (TMPP), and 1,1′-(azodicarbonyl) dipiperidine (ADDP) in the presence of phenol.

Synthesis of functionalized indoles with a trifluoromethyl-substituted stereogenic tertiary carbon atom through an enantioselective Friedel-Crafts alkylation with β-trifluoromethyl-α,β-enones

Chiral complexes of BINOL-based ligands with zirconium tert-butoxide catalyze the Friedel-Crafts alkylation reaction of indoles with β-trifluoromethyl-α,β-unsaturated ketones to give functionalized indoles with an asymmetric tertiary carbon center attached to a trifluoromethyl group. The reaction can be applied to a large number of substituted α-trifluoromethyl enones and substituted indoles. The expected products were obtained with good yields and ees of up to 99%.

Facile conversion of 4,4,4-trifluorobut-2-yn-1-ols to 4,4,4-trifluorobut-2-en-1-ones

Smooth isomerization of 4,4,4-trifluorinated propargylic alcohols 1 opened a new and convenient route to readily get access to the corresponding α,β-unsaturated ketones 4 just by heating a THF solution in the presence of Et3N.