733-53-9

Basic information

• Product Name: p-methoxyphenyl(phenyl)iodonium tetrafluoroborate
• Synonyms: p-methoxyphenyl(phenyl)iodonium tetrafluoroborate
• CAS NO: 733-53-9
• Molecular Weight: 397.947
• Mol File: 733-53-9.mol

Chemical Properties

• CAS DataBase Reference: p-methoxyphenyl(phenyl)iodonium tetrafluoroborate(CAS DataBase Reference)
• NIST Chemistry Reference: p-methoxyphenyl(phenyl)iodonium tetrafluoroborate(733-53-9)
• EPA Substance Registry System: p-methoxyphenyl(phenyl)iodonium tetrafluoroborate(733-53-9)

Safety Data

• Hazardous Substances Data: 733-53-9(Hazardous Substances Data)

Upstream product

• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 109-63-7 boron trifluoride diethyl etherate 
• 5720-07-0 4-methoxyphenylboronic acid 
• 696-62-8 para-iodoanisole 
• 98-80-6 phenylboronic acid 
• 591-50-4 iodobenzene 
• 16308-16-0 1-(diacetoxyiodo)-4-methylbenzene 
• 100-66-3 methoxybenzene 
• 536-80-1 iodosylbenzene 

Downstream Products

• 613-37-6 4-methoxylbiphenyl 
• 611-94-9 4-Methoxybenzophenone 
• 15970-74-8 furan-2-yl(4-methoxyphenyl)methanone 
• 4160-63-8 2-(4-methoxybenzoyl)thiophene 
• 4181-97-9 phenyl 4-methoxybenzoate 
• 80290-29-5 2-phenyl-3-(1-phenylvinyl)oxirane 
• 17113-31-4 2-(4-methoxyphenyl)furan 
• 42545-43-7 2-(4-methoxyphenyl)thiophene 
• 91-01-0 1,1-Diphenylmethanol 
• 696-62-8 para-iodoanisole 
• 720-44-5 1-(4-methoxyphenyl)-1-phenylmethanol 
• 100-66-3 methoxybenzene 
• 720-75-2 methyl 4-phenylbenzoate 
• 729-17-9 methyl 4-(4'-methoxyphenyl)benzoate 

Relevant articles and documents

Unsymmetrical diaryliodonium phenyltrifluoroborate salts: Synthesis, structure and fluorination

The unprecedented reaction of organotrifluoroborates salts of unsymmetrical diaryliodoniums to give aryl fluorides is presented. This preliminary report describes the first synthesis of unsymmetrical diaryliodonium phenyltrifluoroborates along with an exe

Generation of Aryl Radicals through Reduction of Hypervalent Iodine(III) Compounds with TEMPONa: Radical Alkene Oxyarylation

A novel method for selective generation of aryl radicals from diaryliodonium salts and iodanylidene malonates with sodium 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPONa) as a single-electron transfer (SET) reducing reagent is described. In the presence of various alkenes, aryl radicals formed after SET-reduction of hypervalent iodine compounds undergo alkene addition and the adduct radicals that are thus generated are efficiently trapped by the concomitantly generated TEMPO radical to eventually afford oxyarylated products in moderate to very good yields. The efficiency of aryl radical generation of various iodine(III) reagents is studied and the generation of an iodanylidene malonate aryl radical is also investigated by computational methods.

LCopper-catalyzed diarylation of activated alkenes with diaryliodonium salts

Cu(OTf)2-catalyzed diarylation of activated alkenes by using diaryliodonium(III) salts has been developed. With this method, arylated oxindoles can be easily accessed in good yields. Insights into the mechanism of copper-catalyzed arylations are discussed, and the findings are expected to help increase the level of understanding of catalytic arylations with diaryliodonium salts. Georg Thieme Verlag Stuttgart. New York.

Regiospecific one-pot synthesis of diaryliodonium tetrafluoroborates from arylboronic acids and aryl iodides

(Chemical Equation Presented) Diaryliodonium salts have recently received considerable attention as mild arylation reagents in organic synthesis. This paper describes a regiospecific, sequential one-pot synthesis of symmetrical and unsymmetrical diaryliodonium tetrafluoroborates, which are the most popular salts in metal-catalyzed arylations. The protocol is fast and high-yielding and has a large substrate scope. Furthermore, the corresponding diaryliodonium triflates can conveniently be obtained via an in situ anion exchange.

Chromium(ii)-mediated reactions of iodonium tetrafluoroborates with aldehydes: Umpolung of reactivity of diaryl-, alkenyl(aryl)-, and alkynyl(aryl)iodonium tetrafluoroborates

The method described herein allows us, for the first time, to perform umpolung of reactivity of diaryl-, alkenyl(aryl)-, and alkynyl(aryl)iodonium tetrafluoroborates. The method involves generation of organochromium(III) species via reaction of iodonium salts with anhydrous chromium dichloride, followed by their nucleophilic addition to aldehydes to yield alcohols. In contrast to the reaction of aryl and alkenyl halides with chromium dichloride, these iodonium salts are so active that organochromium(III) could be generated without using a nickel catalyst. Substituent effects of unsymmetrically substituted diaryliodonium salts on the product profiles are in good agreement with the reported mode of decomposition of the intermediate unsymmetrical diaryliodanyl radicals. Alkenyl(mesityl)iodonium tetrafluoroborates undergo exclusive alkenylation of aldehydes with no signs of the formation of an arylation product.

Phenyliodine(III) sulfate as a new reagent for synthesis of diaryliodonium salts

Phenyliodine(lll) sulfate (1), prepared from iodosylbenzene and sulfur trioxide, reacts with aromatic compounds under mild conditions to give diaryliodonium salts 2.