Dilute Hydrofluoric Acid as a Fluorinating Agent: Iodofluorination of Olefins with Dilute Hydrofluoric Acid, N -Iodosuccinimide, and a Phase Transfer Catalyst

Manabu Kuroboshi; Tamejiro Hiyama

doi:10.1055/s-1991-20672

Dilute Hydrofluoric Acid as a Fluorinating Agent: Iodofluorination of Olefins with Dilute Hydrofluoric Acid, N -Iodosuccinimide, and a Phase Transfer Catalyst

Manabu Kuroboshi
, Tamejiro Hiyama

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

Abstract

Regio-, stereo-, and chemoselective iodofluorination of olefins is readily effected under a two-phase system using dilute hydrofluoric acid, N-iodosuccinimide, and tetrabutylammonium fluoride as a phase transfer catalyst. Additional use of potassium hydrogen fluoride (KHF ₂ ) enhanced the yields of fluoro-iodo adducts and suppressed the formation of iodohydrins as byproducts.

Original language	English
Pages (from-to)	185-186
Number of pages	2
Journal	Synlett
Volume	1991
Issue number	3
DOIs	https://doi.org/10.1055/s-1991-20672
Publication status	Published - Mar 1991
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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10.1055/s-1991-20672

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abstract = " Regio-, stereo-, and chemoselective iodofluorination of olefins is readily effected under a two-phase system using dilute hydrofluoric acid, N-iodosuccinimide, and tetrabutylammonium fluoride as a phase transfer catalyst. Additional use of potassium hydrogen fluoride (KHF 2 ) enhanced the yields of fluoro-iodo adducts and suppressed the formation of iodohydrins as byproducts.",

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N2 - Regio-, stereo-, and chemoselective iodofluorination of olefins is readily effected under a two-phase system using dilute hydrofluoric acid, N-iodosuccinimide, and tetrabutylammonium fluoride as a phase transfer catalyst. Additional use of potassium hydrogen fluoride (KHF 2 ) enhanced the yields of fluoro-iodo adducts and suppressed the formation of iodohydrins as byproducts.

AB - Regio-, stereo-, and chemoselective iodofluorination of olefins is readily effected under a two-phase system using dilute hydrofluoric acid, N-iodosuccinimide, and tetrabutylammonium fluoride as a phase transfer catalyst. Additional use of potassium hydrogen fluoride (KHF 2 ) enhanced the yields of fluoro-iodo adducts and suppressed the formation of iodohydrins as byproducts.

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Dilute Hydrofluoric Acid as a Fluorinating Agent: Iodofluorination of Olefins with Dilute Hydrofluoric Acid, N -Iodosuccinimide, and a Phase Transfer Catalyst

Abstract

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