41605-53-2

Upstream product

• 375-72-4 Nonafluorobutanesulfonyl fluoride 
• 99-76-3 methyl 4-hydroxylbenzoate 
• 27739-17-9 (4-methoxycarbonylphenoxy)trimethylsilane 

Downstream Products

• 197172-67-1 N-(4-methoxycarbonylphenyl)-n-hexylamine 
• 619-50-1 4-nitrobenzoic acid methyl ester 
• 1198293-87-6 methyl 4-(N-hexylcyclopropanecarboxamido)benzoate 
• 1198293-85-4 methyl 4-(N-butylacetamido)benzoate 
• 5032-55-3 (4-methoxycarbonylphenyl)diphenylphosphine oxide 
• 1198293-95-6 methyl 4-(N-phenethylpyrrolidine-1-carboxamido)benzoate 
• 4058-18-8 methyl 4-(phenylamino)benzoate 
• 23676-05-3 4-morpholin-4-yl-benzoic acid methyl ester 
• 5032-51-9 methyl 4-(diphenylphosphino)benzoate 

Relevant academic research and scientific papers

Palladium-Catalyzed C-P Bond-Forming Reactions of Aryl Nonaflates Accelerated by Iodide

An iodide-accelerated, palladium-catalyzed C-P bond-forming reaction of aryl nonaflates is described. The protocol was optimized for the synthesis of aryl phosphine oxides and was found to be tolerant of a wide range of aryl nonaflates. The general nature of this transformation was established with coupling to other P(O)H compounds for the synthesis of aryl phosphonates and an aryl phosphinate. The straightforward synthesis of stable, isolable aryl nonaflates, in combination with the rapid C-P bond-forming reaction allows facile preparation of aryl phosphorus target compounds from readily available phenol starting materials. The synthetic utility of this general strategy was demonstrated with the efficient preparation of an organic light-emitting diode (OLED) material and a phosphonophenylalanine mimic.

Palladium-Catalyzed Amination of Aryl Nonaflates

The first detailed study of the palladium-catalyzed amination of aryl nonaflates is reported. Use of ligands 2-4 and 6 allows for the catalytic amination of electron-rich and -neutral aryl nonaflates with both primary and secondary amines. With use of Xantphos 5, the catalytic amination of a variety of functionalized aryl nonaflates resulted in excellent yields of anilines; even 2-carboxymethyl aryl nonaflate is effectively coupled with a primary alkylamine. Moderate yields were obtained when coupling halo-aryl nonaflates with a variety of amines, where in most cases the aryl nonaflate reacted in preference to the aryl halide. Overall, aryl nonaflates are an effective alternative to triflates in palladium-catalyzed C-N bond-forming processes due to their increased stability under the reaction conditions.