Improving alkynyl(aryl)iodonium salts: 2-anisyl as a superior aryl group

David J. Hamnett, Wesley J. Moran

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

The majority of alkynyl(aryl)iodonium salts reported in the literature are derived from iodobenzene. This article describes the effects of varying this iodoarene building block on the synthesis, reactivity and stability of these salts. Two procedures to synthesize a variety of known and novel alkynyl(aryl)iodonium tosylates directly from the iodoarene are reported. In the reactions of these salts, those derived from 2-iodoanisole gave superior results than the others tested in every reaction. Isothermal microcalorimetry indicated that these novel salts were significantly more stable and less prone to decomposition than all of the other derivatives.
LanguageEnglish
Pages4156-4162
Number of pages7
JournalOrganic and Biomolecular Chemistry
Volume12
Issue number24
DOIs
Publication statusPublished - 6 May 2014

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Cite this

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title = "Improving alkynyl(aryl)iodonium salts: 2-anisyl as a superior aryl group",
abstract = "The majority of alkynyl(aryl)iodonium salts reported in the literature are derived from iodobenzene. This article describes the effects of varying this iodoarene building block on the synthesis, reactivity and stability of these salts. Two procedures to synthesize a variety of known and novel alkynyl(aryl)iodonium tosylates directly from the iodoarene are reported. In the reactions of these salts, those derived from 2-iodoanisole gave superior results than the others tested in every reaction. Isothermal microcalorimetry indicated that these novel salts were significantly more stable and less prone to decomposition than all of the other derivatives.",
keywords = "Sulfur compounds, Synthesis (chemical), Alkynyls, Aryl group, Building blockes, Iodobenzene, Iodonium, Iodonium salts, Isothermal microcalorimetry, Salts",
author = "Hamnett, {David J.} and Moran, {Wesley J.}",
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language = "English",
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pages = "4156--4162",
journal = "Organic and Biomolecular Chemistry",
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publisher = "Royal Society of Chemistry",
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}

Improving alkynyl(aryl)iodonium salts: 2-anisyl as a superior aryl group. / Hamnett, David J.; Moran, Wesley J.

In: Organic and Biomolecular Chemistry, Vol. 12, No. 24, 06.05.2014, p. 4156-4162.

Research output: Contribution to journalArticle

TY - JOUR

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AU - Hamnett, David J.

AU - Moran, Wesley J.

PY - 2014/5/6

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N2 - The majority of alkynyl(aryl)iodonium salts reported in the literature are derived from iodobenzene. This article describes the effects of varying this iodoarene building block on the synthesis, reactivity and stability of these salts. Two procedures to synthesize a variety of known and novel alkynyl(aryl)iodonium tosylates directly from the iodoarene are reported. In the reactions of these salts, those derived from 2-iodoanisole gave superior results than the others tested in every reaction. Isothermal microcalorimetry indicated that these novel salts were significantly more stable and less prone to decomposition than all of the other derivatives.

AB - The majority of alkynyl(aryl)iodonium salts reported in the literature are derived from iodobenzene. This article describes the effects of varying this iodoarene building block on the synthesis, reactivity and stability of these salts. Two procedures to synthesize a variety of known and novel alkynyl(aryl)iodonium tosylates directly from the iodoarene are reported. In the reactions of these salts, those derived from 2-iodoanisole gave superior results than the others tested in every reaction. Isothermal microcalorimetry indicated that these novel salts were significantly more stable and less prone to decomposition than all of the other derivatives.

KW - Sulfur compounds

KW - Synthesis (chemical)

KW - Alkynyls

KW - Aryl group

KW - Building blockes

KW - Iodobenzene

KW - Iodonium

KW - Iodonium salts

KW - Isothermal microcalorimetry

KW - Salts

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DO - 10.1039/c4ob00556b

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EP - 4162

JO - Organic and Biomolecular Chemistry

T2 - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

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