68295-44-3

Upstream product

• 108-88-3 toluene 
• 1711-07-5 3-fluorobenzoyl chloride 
• 17318-03-5 bromo(3-fluorophenyl)magnesium 
• 104-87-0 4-methyl-benzaldehyde 
• 366-43-8 3-fluorobenzoic acid phenyl ester 
• 5720-05-8 4-methylphenylboronic acid 
• 99-94-5 p-Toluic acid 
• 36228-65-6 2-pyridyl 4-methylbenzoate 
• 768-35-4 3-fluorophenylboronic acid 
• 874-60-2 4-methyl-benzoyl chloride 
• 455-38-9 3-fluorobenzoic acid 

Downstream Products

• 186094-12-2 4-[Chloro-(3-fluoro-phenyl)-methyl]-N,N-diethyl-benzamide 
• 186094-08-6 N,N-Diethyl-4-[(3-fluoro-phenyl)-hydroxy-methyl]-benzamide 
• 186094-04-2 N,N-Diethyl-4-(3-fluoro-benzoyl)-benzamide 
• 1026331-02-1 4-(3-Fluoro-benzoyl)-benzoyl chloride 
• 186094-02-0 4-(3-fluorobenzoyl)benzoic acid 

Relevant academic research and scientific papers

Suzuki-Miyaura cross-coupling of esters by selective O-C(O) cleavage mediated by air- And moisture-stable [Pd(NHC)(μ-Cl)Cl]2precatalysts: Catalyst evaluation and mechanism

The cross-coupling of aryl esters has emerged as a powerful platform for the functionalization of otherwise inert acyl C-O bonds in chemical synthesis and catalysis. Herein, we report a combined experimental and computational study on the acyl Suzuki-Miyaura cross-coupling of aryl esters mediated by well-defined, air- and moisture-stable Pd(ii)-NHC precatalysts [Pd(NHC)(μ-Cl)Cl]2. We present a comprehensive evaluation of [Pd(NHC)(μ-Cl)Cl]2 precatalysts and compare them with the present state-of-the-art [(Pd(NHC)allyl] precatalysts bearing allyl-type throw-away ligands. Most importantly, the study reveals [Pd(NHC)(μ-Cl)Cl]2 as the most reactive precatalysts discovered to date in this reactivity manifold. The unique synthetic utility of this unconventional O-C(O) cross-coupling is highlighted in the late-stage functionalization of pharmaceuticals and sequential chemoselective cross-coupling, providing access to valuable ketone products by a catalytic mechanism involving Pd insertion into the aryl ester bond. Furthermore, we present a comprehensive study of the catalytic cycle by DFT methods. Considering the clear advantages of [Pd(NHC)(μ-Cl)Cl]2 precatalysts on several levels, including facile one-pot synthesis, superior atom-economic profile to all other Pd(ii)-NHC catalysts, and versatile reactivity, these should be considered as the 'first-choice' catalysts for all routine applications in ester O-C(O) bond activation.

Heterogeneous Suzuki-Miyaura coupling of heteroaryl ester: Via chemoselective C(acyl)-O bond activation

A site-selective supported palladium nanoparticle catalyzed Suzuki-Miyaura cross-coupling reaction with heteroaryl esters and arylboronic acids as coupling partners was developed. This methodology provides a heterogeneous catalytic route for aryl ketone formation via C(acyl)-O bond activation of esters by successful suppression of the undesired decarbonylation phenomenon. The catalyst can be reused and shows high activity after eight cycles. The XPS analysis of the catalyst before and after the reaction suggested that the reaction might be performed via a Pd0/PdII catalytic cycle that began with Pd0.

Experimental Evaluation of (L)Au Electron-Donor Ability in Cationic Gold Carbene Complexes

29Si NMR spectroscopy was employed to evaluate the electron donor properties of the (L)Au fragments in the cationic gold (β,β-disilyl)vinylidene complexes [(L)Au=C=CSi(Me)2CH2CH2Si(Me)2]+B(C6F5)4? [L=P(tBu)2o-biphenyl or NHC] relative to the p-substituted aryl group in the α-aryl-(β,β-disilyl)vinyl cations [(p-C6H4X)-C= CSi(Me)2CH2CH2Si(Me)2]+B(C6F5)4?. Similarly, 19F NMR was employed to evaluate the σ- and π-electron donor properties of the (L)Au fragments in the neutral gold fluorophenyl complexes (L)Au(C6H4F) and in the cationic (fluorophenyl)methoxycarbene complexes [(L)AuC(OMe)(C6H4F)]+SbF6? [L=P(tBu)2o-biphenyl or IPr] relative to the p-substituted aryl group of the protonated monofluorobenzophenones [(p-C6H4X)(C6H4F)COH]+OTf?. The results of these studies indicate that relative to p-substituted aryl groups, the gold (L)Au fragments [L=P(tBu)2o-biphenyl or NHC] are significantly more inductively electron donating and are comparable π-donors and for this reason, the extent of (L)Au→C1 electron donation in gold carbene complexes appears to exceed that provided by a p-(dimethyamino)phenyl group. Furthermore, the [L=P(tBu)2o-biphenyl]Au fragment is a nominally stronger electron donor than the (IPr)Au fragment, and both are significantly more inductively electron donating than the (PPh3)Au and [P(OMe)3]Au fragments.

Discovery of trypanocidal thiosemicarbazone inhibitors of rhodesain and TbcatB

Human African trypanosomiasis (HAT) is caused by the protozoan parasite Trypanosoma brucei. The cysteine proteases of T. brucei have been shown to be crucial for parasite replication and represent an attractive point for therapeutic intervention. Herein we describe the synthesis of a series of thiosemicarbazones and their activity against the trypanosomal cathepsins TbcatB and rhodesain, as well as human cathepsins L and B. The activity of these compounds was determined against cultured T. brucei, and specificity was assessed with a panel of four mammalian cell lines.

Probes for narcotic receptor mediated phenomena. 23. Synthesis, opioid receptor binding, and bioassay of the highly selective δ agonist (+)-4- [(αR)-α-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-methoxybenzyl]N,N- diethylbenzamide (SNC 80) and related novel nonpeptide δ opioid receptor ligands

The highly selective delta (δ) opioid receptor agonist SNC 80 [(+)-4- [(αR)-α-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-methoxybenzyl]-N,N- diethylbenzamide, (+)-21] and novel optically pure derivatives were synthesized from the enantiomers of 1-allyl-trans-2,5-dimethylpiperazine (2). The piperazine (±)-2 was synthesized, and its enantiomers were obtained on a multigram scale in >99% optical purity by optical resolution of the racemate with the camphoric acids. The absolute configuration of (+)-2 was determined to be 2S,5R by X-ray analysis of the salt with (+)-camphoric acid. Since the chirality of the starting material was known, and the relative configuration of compounds (-)-21, (-)-22, and (+)-23 were obtained by single-crystal X- ray analysis, the assignment of the absolute stereochemistry of the entire series could be made. Radioreceptor binding studies in rat brain preparations showed that methyl ethers (+)-21 (SNC 80) and (-)-25 exhibited strong selectivity for rat δ receptors with low nanomolar affinity to 6 receptors and only micromolar affinity for rat mu (μ) opioid receptors. Compounds (- )-21, (-)-22, and (-)-23 showed micromolar affinities for δ opioid receptors. The unsubstituted derivative (+)-22 and the fluorinated derivative (-)-27 showed >2659- and >2105-fold δ/μ binding selectivity, respectively. The latter derivatives are the most selective ligands described in the new series. Studies with some of the compounds described in the isolated mouse vas deferens and guinea pig ileum bioassays revealed that all were agonists with different degrees of selectivity for the δ opioid receptor. These data show that (+)-21 and (+)-22 are potent δ receptor agonists and suggest that these compounds will be valuable tools for further study of the δ opioid receptor at the molecular level, including its function and role in analgesia and drug abuse.