Concepedia

Synthesis of ethynyl(phenyl)iodonium tetrafluoroborate. A new reagent for ethynylation of 1,3-dicarbonyl compounds

Masahito Ochiai, Takao Ito, Yoshikazu Takaoka, Yukio Masaki, Munetaka Kunishima, Shohei Tani, Yoshimitsu Nagao

Journal of the Chemical Society Chemical Communications · 1990 · 114 citations · 14 references

DOI

Concepts

Abstract

Hydrogen fluoride-induced protiodetrimethylsilylation of trimethylsilylethynyl(phenyl)iodonium tetrafluoroborate (5), prepared from bis(trimethylsilyl)ethyne (4), affords ethynyl(phenyl)iodonium tetrafluoroborate (1), a reagent for α-ethynylation of β-dicarbonyl compounds under mild conditions.

References

14

Tandem Michael-carbene insertion reactions of alkynyliodonium salts. Extremely efficient cyclopentene annulations

Masahito Ochiai, Munetaka Kunishima, Yoshimitsu Nagao et al. · Journal of the American Chemical Society · 1986 · 150 citations

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Acetylenic and Ethylenic Iodonium Salts and Their Reactions with a Carbanion<sup>1,2</sup>

F. Marshall Beringer, Suzanne A. Galton · The Journal of Organic Chemistry · 1965 · 94 citations

, , +5

Alkynylaryliodonium tosylates and aryl[.beta.-(tosyloxy)vinyl]iodonium tosylates from reactions of terminal alkynes with [hydroxy(tosyloxy)iodo]benzene

Louis Rebrovic, Gerald F. Koser · The Journal of Organic Chemistry · 1984 · 92 citations

, , +8

Chloroacetylenes as Michael acceptors. 3. Mechanism and synthetic utility of enolate reactions with halogenated olefins and chloroacetylenes

Andrew S. Kende, Pawel Fludzinski, John H. Hill · Journal of the American Chemical Society · 1984 · 86 citations

, , +5

Intramolecular carbon-hydrogen insertions of alkylidenecarbenes. I. Selectivity

John Gilbert, David H. Giamalva, Upali Weerasooriya · The Journal of Organic Chemistry · 1983 · 78 citations

, , +8