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

Dixon, Luke I.; Carroll, Michael A.; Ellames, George J.; Gregson, Thomas J.

doi:10.1002/0471264229.os091.06

Cited by 2 publications

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“…Alkynyliodonium salts are generally prepared by the reaction of a hypervalent iodine reagent with terminal alkynes, ,− or silylated, − stannylated, − and borylated alkynes. − A one-pot procedure for preparing alkynyliodonium salts from alkynyl precursors and iodoarenes and m CPBA has been developed. ,, The crystal structure of alkynyl(aryl)iodonium salts has been characterized by X-ray crystallography, ,,,− and it has been demonstrated that the aryl group occupies an equatorial position, whereas the alkynyl moiety and the counterion occupy apical positions. The thermal stability of alkynyl(aryl)iodonium salts depends on the nature of the anion and the substituent on the acetylenic β-carbon.…”

Section: Synthetic Applications Of Trivalent Iodine Compoundsmentioning

confidence: 99%

Advances in Synthetic Applications of Hypervalent Iodine Compounds

2016

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The preparation, structure, and chemistry of hypervalent iodine compounds are reviewed with emphasis on their synthetic application. Compounds of iodine possess reactivity similar to that of transition metals, but have the advantage of environmental sustainability and efficient utilization of natural resources. These compounds are widely used in organic synthesis as selective oxidants and environmentally friendly reagents. Synthetic uses of hypervalent iodine reagents in halogenation reactions, various oxidations, rearrangements, aminations, C−C bond-forming reactions, and transition metal-catalyzed reactions are summarized and discussed. Recent discovery of hypervalent catalytic systems and recyclable reagents, and the development of new enantioselective reactions using chiral hypervalent iodine compounds represent a particularly important achievement in the field of hypervalent iodine chemistry. One of the goals of this Review is to attract the attention of the scientific community as to the benefits of using hypervalent iodine compounds as an environmentally sustainable alternative to heavy metals.

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