42096-33-3

Upstream product

• 16419-60-6 2-Methylphenylboronic acid 
• 29420-49-3 potassium nonaflate 
• 375-72-4 Nonafluorobutanesulfonyl fluoride 
• 4549-72-8 sodium o-cresolate 
• 95-48-7 ortho-cresol 

Downstream Products

• 1205-39-6 N-phenyl-2-methylaniline 
• 6840-26-2 diphenyl-o-tolyl-phosphine oxide 
• 130250-61-2 2-methyl-N-methoxy-N-methylbenzamide 
• 1255365-30-0 2-methyl-N-morpholinobenzenesulfonamide 
• 80-28-4 N-(2-methylphenyl)-p-toluenesulphonamide 
• 1262210-33-2 (Z)-1-methyl-2-(1-phenylbut-1-en-1-yl)benzene 
• 83135-54-0 (E)-1-methyl-2-(3-phenylprop-1-en-1-yl)benzene 
• 1985-77-9 (Z)-(1-(o-tolyl)ethene-1,2-diyl)dibenzene 
• 1262210-27-4 2-methoxy-2'-methyl-2,3,4,5-tetrahydro-1,1'-biphenyl 
• 1262210-32-1 (Z)-1-(1-(4-methoxyphenyl)prop-1-en-1-yl)-2-methylbenzene 
• 54560-76-8 N-(2-methylphenyl)-n-hexylamine 
• 108-88-3 toluene 

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.

Bismuth-Catalyzed Oxidative Coupling of Arylboronic Acids with Triflate and Nonaflate Salts

Herein we present a Bi-catalyzed cross-coupling of arylboronic acids with perfluoroalkyl sulfonate salts based on a Bi(III)/Bi(V) redox cycle. An electron-deficient sulfone ligand proved to be key for the successful implementation of this protocol, which allows the unusual construction of C(sp2)-O bonds using commercially available NaOTf and KONf as coupling partners. Preliminary mechanistic studies as well as theoretical investigations reveal the intermediacy of a highly electrophilic Bi(V) species, which rapidly eliminates phenyl triflate.

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.

Synthesis of polysubstituted olefins by Pd-catalyzed cross-coupling reaction of tosylhydrazones and aryl nonaflates

Aryl nonaflates are employed as electrophiles in the Pd-catalyzed cross-coupling with tosylhydrazones affording di-, tri-, and tetrasubstituted olefins. Fine tunning of the reaction conditions are required to accomplish the coupling successfully, includin

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.