Alkynyliodonium Triflates Research Articles

Synthesis of Alkynyliodonium Salts: Preparation of Phenyl(phenylethynyl)iodonium Trifluoroacetate

Alkynyliodonium salts are highly versatile reactive intermediates and as such, have been used in a number of cycloaddition reactions including 1,3-dipolar cycloadditions with nitrile-oxides, diazoketones and azides as well as Diels-Alder chemistry. This article discusses the preparation procedure of phenyl(phenylethynyl)iodonium trifluoroacetate. Keywords: Phenyl(phenylethynyl)iodonium trifluoroacetate; Alkynyliodonium tosylates; Alkynyliodonium triflates; Stang's reagent; Koser's Reagent

ChemInform Abstract: Novel Cations and Molecules from Phosphaalkynes, 1H-Phosphirenes and from Tetraphosphacubane

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

An Efficient Ligand Exchange Reaction of (E)-[(β-(Trifluoromethanesulfonyloxy)ethenyl](phenyl)iodonium Triflates with Aryl- and Alkynyllithium Reagents Leading to Diaryl- and Alkynyliodonium Triflates

An Efficient Ligand Exchange Reaction of (E)-[(β-(Trifluoromethanesulfonyloxy)ethenyl](phenyl)iodonium Triflates with Aryl- and Alkynyllithium Reagents Leading to Diaryl- and Alkynyliodonium Triflates

Novel Cations and Molecules from Phosphaalkynes, 1H-Phosphirenes and from Tetraphosphacubane

Generation and trapping (counter ion) of the phosphavinyl cation (the P-analog of vinyl cation) by low temperature protonation of kinetically stable phosphaalkynes in super acid media led to the formation of the corresponding phosphaalkenes without direct observation of a long-lived cation. Reactions of RCP (R = tBu, 1-Ad) with “PhSeF” and with PhSeCl resulted in bis-phenylselenenylation and chlorophenylselenenylation respectively, forming novel Se-containing phosphaalkenes. Ionization of 1-H-triflato-phosphirene with B(OTf) 3 /SO2 led to the direct observation of a persistent phosphirenylium cation. The (CO)5 W-complexed phosphirenylium cation was subsequently generated from the (CO)5 W-complexed triflate and trifluoroacetate derivatives. Progress in P-functionalization of tetraphosphacubane by reactions with potent electrophiles (i.e. MeOTf, EtOTf“PhCH2OTf”, TMSCH2OTf), alkynyl-iodonium triflates and with protic superacids are briefly summarized.

ChemInform Abstract: Ready Formation of Functionalized Alkynyl Phenyl Selenides and Tellurides via Alkynyliodonium Triflates.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Ready Formation of Functionalized Alkynyl Phenyl Selenides and Tellurides Via Alkynyliodonium Triflates

Ready Formation of Functionalized Alkynyl Phenyl Selenides and Tellurides Via Alkynyliodonium Triflates

ChemInform Abstract: Inter‐ and Intramolecular Addition/Cyclizations of Sulfonamide Anions with Alkynyliodonium Triflates. Synthesis of Dihydropyrrole, Pyrrole, Indole, and Tosylenamide Heterocycles.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

1-(Organosulfonyloxy)-3(1H)-1,2-benziodoxoles: Preparation and Reactions with Alkynyltrimethylsilanes.

Organosulfonyloxy derivatives of 1,2-benziodoxol-3(1H)-one (3a-c) and 3,3-bis(trifluoromethyl)-3(1H)-1,2-benziodoxole (5a-c) can be prepared in high yield by the reaction of 1-hydroxybenziodoxoles 1 or 4 and the corresponding sulfonic acids or Me(3)SiOTf in the form of stable, but moderately hygroscopic, microcrystalline solids. Reaction of the triflate derivatives 3a and 5a with alkynyltrimethylsilanes affords either alkynyliodonium triflates 6, or (E)-beta-(trifluoromethanesulfonyloxy)alkenyliodonium triflates 7, while the same reaction in the presence of pyridine selectively gives the respective 1-alkynylbenziodoxoles 8 and 9 in 82-90% yield.

Inter- and Intramolecular Addition/Cyclizations of Sulfonamide Anions with Alkynyliodonium Triflates. Synthesis of Dihydropyrrole, Pyrrole, Indole, and Tosylenamide Heterocycles

The synthesis of dihydropyrroles, pyrroles, and indoles through [3-atom + 2-atom] combination of ethyl or aryl tosylamide anions with phenyl(propynyl)iodonium triflate, and the base-mediated intramolecular bicyclization of alkynyliodonium-bearing tosylamide or tosylimide substrates to furnish bicyclic and tricyclic tosylenamide (-enimide) products, is described. A detailed discussion of the scope, limitations, byproduct formation, and the basis for observed diastereoselectivity is presented.

A novel hypervalent iodine reagent prepared from o-iodosylbenzoic acid and trifluoromethanesulfonic acid preparation and reactions of alkynyl( o-carboxyphenyl)iodonium triflates

A hyervalent iodine reagent prepared from o-iodosylbenzoic acid and trifluoromethanesulfonic acid (TfOH) (1:2) showed a high reactivity toward aromatic substrates, giving aryl( o-carboxyphenyl)iodonium triflates in good to high yields. Treatment of the iodine reagent with 1-trimethylsilylalkynes afforded alkynyliodonium triflates bearing carboxy group in high yields. The alkynyliodonium triflates indicated a high efficiency as a Michael acceptor to nucleophiles and the o-carboxyphenyliodonio group behaved as a good leaving group.