65488-27-9

Upstream product

• 120579-20-6 methyl 4-((diethoxyphosphoryl)oxy)benzoate 
• 1066-45-1 trimethyltin(IV)chloride 
• 661-69-8 hexamethyldistannane 
• 3795-79-7 methyl 4-(methylthio)benzoate 
• 6302-65-4 methyl 4-mercaptobenzoate 
• 7377-26-6 4-Methoxycarbonylbenzoyl chloride 
• 709-69-3 methyl 4-(fluorocarbonyl) benzoate 
• 619-45-4 4-methoxycarbonyl aniline 
• 610-96-8 methyl chlorobenzoate 
• 1126-46-1 Methyl 4-chlorobenzoate 
• 619-44-3 methyl 4-iodobenzoate 

Downstream Products

• 720-75-2 methyl 4-phenylbenzoate 
• 1132711-33-1 methyl 4-(7-bromo-5,6-benzo[c][1,2,5]thiadiazol-4-yl)benzoate 
• 153881-22-2 N-[2-(2-Amino-ethoxy)-ethyl]-4-(2-hydroxy-4-phenyl-cyclohexyl)-benzamide 
• 197777-76-7 4-(2-Hydroxy-4-phenyl-cyclohexyl)-benzoic acid 
• 153881-23-3 4-(4-Phenyl-cyclohex-1-enyl)-benzoic acid methyl ester 

Relevant academic research and scientific papers

Synthesis of Arylstannanes via Palladium-Catalyzed Decarbonylative Coupling of Aroyl Fluorides

Aryl stannanes are valuable precursors in organic transformations, but their synthetic methods are limited. Here we present a Pd-catalyzed decarbonylative stannylation of acid fluorides in the absence of exogenous base. Various aryl stannanes were efficiently prepared from bench-stable transition metal catalyst and ligand with broad functional group compatibility and substrate scope including natural products and pharmaceuticals. This protocol was also successfully used to a late-stage diversification of an existing uricosuric drug probenecid. (Figure presented.).

Transition-Metal-Free Aryl-Heteroatom Bond Formation via C-S Bond Cleavage

Aryl-heteroatom bonds (C-Het) are almost ubiquitously present in chemical molecules. However, methods for diverse C-Het bond formations from a simple substrate are limited. Herein, we report a convenient and efficient C-S bond transformation of aryl sulfoniums to various C-Het bonds (C-O, C-S, C-Sn, C-Si, C-Se) in the absence of any transition-metal catalyst. These reactions proceeded in mild conditions with a wide substrate scope.

Synthesis of Aryl Trimethylstannane via BF3·OEt2-Mediated Cross-Coupling of Hexaalkyl Distannane Reagent with Aryl Triazene at Room Temperature

BF3·OEt2-mediated cross-coupling of (SnMe3)2 with aryl triazene offers a new strategy for the synthesis of aryl stannane. A variety of synthetically useful aryl trimethylstannanes were produced in moderate to good yields with this metal-free approach. One-pot sequential Stille cross-coupling with different aryl bromides provides a short entry to both symmetrical and unsymmetrical biaryl compounds.

A practical method for the preparation of 18F-labeled aromatic amino acids from nucleophilic [18F]fluoride and stannyl precursors for electrophilic radiohalogenation

In a recent contribution of Scott et al., the substrate scope of Cu-mediated nucleophilic radiofluorination with [18F]KF for the preparation of 18F-labeled arenes was extended to aryland vinylstannanes. Based on these findings, the potential of this reaction for the production of clinically relevant positron emission tomography (PET) tracers was investigated. To this end, Cu-mediated radiofluorodestannylation using trimethyl(phenyl)tin as a model substrate was re-evaluated with respect to different reaction parameters. The resulting labeling protocol was applied for 18F-fluorination of different electron-rich, -neutral and -poor arylstannyl substrates in RCCs of 16-88%. Furthermore, this method was utilized for the synthesis of 18F-labeled aromatic amino acids from additionally N-Boc protected commercially available stannyl precursors routinely applied for electrophilic radiohalogenation. Finally, an automated synthesis of 6-[18F]fluoro-L-m-tyrosine (6-[18F]FMT), 2-[18F]fluoro-L-tyrosine (2-[18F]F-Tyr), 6-[18F]fluoro-L-3, 4-dihydroxyphenylalanine (6-[18F]FDOPA) and 3-O-methyl-6-[18F]FDOPA ([18F]OMFD) was established furnishing these PET probes in isolated radiochemical yields (RCYs) of 32-54% on a preparative scale. Remarkably, the automated radiosynthesis of 6-[18F]FDOPA afforded an exceptionally high RCY of 54 5% (n = 5).

Dye compounds, and their use in dye-sensitized solar cells

Disclosed are compounds of formula D-B-A-ANC (wherein D is an electron donor group, B is a chromophore group, A is an electron acceptor group, and ANC is an anchoring part comprising at least one anchoring group, and dye-sensitized solar cells (DSSC) incorporating the same as a dye-sensitizer.

Regioselectivity of methyl chlorobenzoate analogues with trimethylstannyl anions by radical nucleophilic substitution: Theoretical and experimental study

Reactions of methyl 2,5-dichlorobenzoate, methyl 4-chlorobenzoate, methyl 2-chlorobenzoate and methyl 3-chlorobenzoate with Me3Sn- ions gave the corresponding substitution products by an SRN1 mechanism. Competition experiments showed that the relative reactivity of chlorine as the leaving group with respect to the ester group in methyl chlorobenzoate is para ≥ ortho ? meta toward Me3Sn- ions. Theoretical studies were able to explain the observed reactivity on the basis of the energetic properties of the transition states of the radical anions formed in these reactions.

Phenols as starting materials for the synthesis of arylstannanes via SRN11

Phenols are converted into aryl diethyl phosphate esters (ArDEP), which on reaction with sodium trimethylstannide (1) or sodium triphenylstannide (2) in liquid ammonia afford arylstannanes by the SRN1 mechanism. Thus, the photostimulated reaction of phenylDEP (3), (4-methoxyphenyl)DEP (4), (4-biphenyl)DEP (5), (1-naphthyl)DEP (6), (2-naphthyl)DEP (7), and 2- (34), 3- (32), and (4-pyridyl)DEP (35) with 1 leads to monostannylated product in fair to excellent yields (20-98%). Also, substrates containing two or three leaving groups react with 1 under irradiation, affording the corresponding di- or tristannylated aryl compounds. With tetraethyl m-phenylene bisphosphate (15), tetraethyl p-phenylene bisphosphate (21), (4-chlorophenyl)DEP (22), and 1,3,5-tris(diethylphospho)benzene (30), the di- or trisubstitution products 1,3-bis(trimethylstannyl)benzene (19) (79%), 1,4-bis(trimethylstannyl)benzene (23) (95 and 97%), and 1,3,5-tris(trimethylstannyl)benzene (31) (57%) are obtained, respectively. Also, the reaction of 6 and 7 with 2 leads to substitution products in quantitative yields, and the reaction of 21, 22, and (4-bromophenyl)DEP (24) with 2 affords 1,4-bis(triphenylstannyl)benzene (38) in high yields (70-100%). On the other hand, the results obtained in the photostimulated reaction of 24 and (4-iodophenyl)DEP (25) with 1, as well as in the reaction of 25 with 2, clearly indicate a fast HME reaction.