32848-24-1

Upstream product

• 120-47-8 Ethyl 4-hydroxybenzoate 
• 375-72-4 Nonafluorobutanesulfonyl fluoride 
• 25628-11-9 phenyl 1,1,2,2,3,3,4,4,4-nonafluoro-1-butanesulfonate 
• 623-49-4 ethyl cyanoformate 
• 199465-44-6 4-iodophenyl nonaflate 

Downstream Products

• 108620-55-9 ethyl 3'-amino-[1,1'-biphenyl]-4-carboxylate 
• 6301-56-0 ethyl 4-phenylbenzoate 
• 93-89-0 benzoic acid ethyl ester 
• 197662-64-9 ethyl 1,2,4,5-tertafluoro-3-methoxybenzene 
• 1352921-98-2 (E)-ethyl 4-(buta-1,3-dien-1-yl)benzoate 
• 1346521-62-7 ethyl 4-(pentan-3-yl)benzoate 
• 451-46-7 4-fluorobenzoic acid ethyl ester 
• 739-33-3 ethyl 4-(4-methylbenzenesulfonamido)benzoate 

Relevant academic research and scientific papers

Practical Ni-Catalyzed Cross-Coupling of Unsaturated Zinc Pivalates with Unsaturated Nonaflates and Triflates

A practical nickel-catalyzed cross-coupling of (hetero)aryl or alkynylzinc pivalates with various unsaturated nonaflates or triflates is described. Organozinc pivalates allow these cross-couplings to take place with high yields and a low catalyst loading (0.5 mol %). Couplings with (E)- and (Z)-alkenyl triflates proceed with retention of configuration.

Barbier–Negishi Coupling of Secondary Alkyl Bromides with Aryl and Alkenyl Triflates and Nonaflates

A mild and practical Barbier–Negishi coupling of secondary alkyl bromides with aryl and alkenyl triflates and nonaflates has been developed. This challenging reaction was enabled by the use of a very bulky imidazole-based phosphine ligand, which resulted in good yields as well as good chemo- and site selectivities for a broad range of substrates at room temperature and under non-aqueous conditions. This reaction was extended to primary alkyl bromides by using an analogous pyrazole-based ligand.

One-pot, two-step, microwave-assisted palladium-catalyzed conversion of aryl alcohols to aryl fluorides via aryl nonaflates

A convenient procedure for converting aryl alcohols to aryl fluorides via aryl nonafluorobutylsulfonates (ArONf) is presented. Moderate to good one-pot, two-step yields were achieved by this nonaflation and microwave-assisted, palladium-catalyzed fluorination sequence. The reductive elimination step was investigated by DFT calculations to compare fluorination with chlorination, proving a larger thermodynamic driving force for the aryl fluoride product. Finally, a key aryl fluoride intermediate for the synthesis of a potent HCV NS3 protease inhibitor was smoothly prepared with the novel protocol.

A general method for palladium-catalyzed reactions of primary sulfonamides with aryl nonaflates

A general method for Pd-catalyzed sulfonamidation of aryl nonafluorobutanesulfonates (aryl nonaflates) is described. A biaryl phosphine ligand, t-BuXPhos, formed the most active catalyst, and K3PO 4 in tert-amyl alcohol was found to be the optimal base-solvent combination for the reaction. The reaction conditions were tolerant of various functional groups such as cyano, nitro, ester, aldehyde, ketone, chloride, carbamate, and phenol. Heterocyclic aryl nonaflates were found to be suitable coupling partners. High yields of the coupled products were obtained from the reactions between inherently disfavored substrates such as electron-rich nonaflates and electron-poor sulfonamides. Kinetic data suggest reductive elimination to be the rate-limiting step for the reaction. The only limitation of this methodology that we have identified is the inability of 2,6-disubstituted aryl nonaflates to efficiently participate in the reaction.