93131-74-9

Upstream product

• 375-72-4 Nonafluorobutanesulfonyl fluoride 
• 150-76-5 4-methoxy-phenol 
• 536-74-3 phenylacetylene 
• 98-80-6 phenylboronic acid 
• 32848-23-0 para-nitrophenyl perfluorobutanesulfonate 

Downstream Products

• 16664-54-3 N-(n-hexyl)-p-methoxyaniline 
• 1208-86-2 N-(4-methoxyphenyl)phenylamine 
• 4663-13-2 1,1-bis(4-methoxyphenyl)propene 
• 856855-30-6 1-ethyl-4-(4-methoxyphenyl)-1,2,3,6-tetrahydropyridine 
• 1262210-26-3 2,4'-dimethoxy-2,3,4,5-tetrahydro-1,1'-biphenyl 
• 914365-66-5 4-(4-methoxyphenyl)-3,6-dihydro-2H-pyran 
• 20758-60-5 1-(4-methoxyphenyl)cyclohexene 
• 18421-23-3 (E)-1-methoxy-4-(pent-2-en-3-yl)benzene 
• 1233-23-4 (Z)-1-(4-methoxyphenyl)-1,2-diphenylethylene 
• 35856-81-6 1-methoxy-4-[(1E)-3-phenylprop-1-en-1-yl]benzene 
• 83248-34-4 1-methoxy-4-(2-methyl-1-phenylprop-1-en-1-yl)benzene 
• 51-66-1 4-methoxyacetanilide 
• 150-76-5 4-methoxy-phenol 
• 100-66-3 methoxybenzene 

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.

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.

Repetitive synthetic method for o, o, p-oligophenylenes using C-H arylation

A synthetic method for the preparation of o,o,p-oligophenylenes has been developed. It involves Miura's C-H arylation of 2-biphenols with aryl nonaflates as the key step. Oligophenylenes with defined lengths are successfully synthesized using this method.

Palladium-catalyzed one-pot cross-coupling of phenols using nonafluorobutanesulfonyl fluoride

Palladium-catalyzed coupling reactions, such as the Suzuki-Miyaura, Sonogashira, Stille, and Buchwald-Hartwig couplings, of phenols using nonafluorobutanesulfonyl fluoride (NfF) are described. These reactions proceeded through the in situ nonaflation of p

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

PMHS-mediated couplings of alkynes or benzothiazoles with various electrophiles: Application to the synthesis of (-)-akolactone A

Polymethylhydrosiloxane (PMHS) in combination with CsF facilitates the cross-coupling of alkynes or benzothiazoles with an array of vinyl, styryl, and aryl halides or nonaflates as well as acid chlorides. Experimental and spectroscopic evidence indicates that these reactions involve the in situ generation of a siloxyl intermediate. These cross-couplings proceed relatively quickly at room temperature and under amine-free conditions. To demonstrate the applicability of the method, a total synthesis of the cyctotoxic butanolide (-)-akolactone A was carried out.

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.

Stille couplings catalytic in tin: The "Sn-O" approach

A one-pot tandem Pd-catalyzed hydrostannylation/Stille coupling protocol for the stereoselective generation of vinyltins and their subsequent union, employing only catalytic amounts of tin, is described. By recycling the organotin halide Stille byproduct back to organotin hydride, a hydrostannylation/cross-coupling sequence can be carried out with catalytic amounts of tin. Such a process is most effective with Me3SnCl serving as the tin source. This protocol allows a 94% reduction of the tin requirement, while maintaining good yields (up to 90%) for a variety of Stille products. Furthermore, since one cycle requires the tin to undergo at least four transformations, each moiety of trialkyltin is experiencing a minimum of 60 reactions over the course of the hydrostannylation/Stille, sequence.

A high throughput synthesis of aryl triflate and aryl nonaflate promoted by a polymer supported base (PTBD)

A rapid synthesis of aryl triflate and aryl nonaflate was developed using 4-nitrophenyl triflate and 4-nitrophenyl nonaflate as perfluoroalkanesulfonyl transfer reagents in combination with a polymer supported base (PTBD). Simple filtration of the reactio