Anion Metathesis of Diaryliodonium Tosylate Salts with a Solid-Phase Column Constructed from Readily Available Laboratory Consumables

Herein, we describe the discovery and development of a method to exchange the counteranion component of diaryliodonium salts, which is a critical step for their use in chemical synthesis. The method involves a reusable and readily available solid-phase column assembled from common laboratory consuma...

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Bibliographic Details
Published inOrganic process research & development Vol. 23; no. 6; pp. 1269 - 1274
Main Authors Gallagher, Rory T, Seidl, Thomas L, Bader, Joshua, Orella, Charles, Vickery, Thomas, Stuart, David R
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.06.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Applied
Chemistry, Organic
Physical Sciences
Science & Technology
anion exchange
solid-phase
diaryliodonium
arylation
MILD SYNTHESIS
ACID
ONE-POT SYNTHESIS
SCOPE
ARENES
IODINE
EXCHANGE
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Summary:Herein, we describe the discovery and development of a method to exchange the counteranion component of diaryliodonium salts, which is a critical step for their use in chemical synthesis. The method involves a reusable and readily available solid-phase column assembled from common laboratory consumables. This process avoids challenging product separation associated with other methods for anion metathesis of diaryliodonium salts, and selected examples demonstrate the scope of the method. Hazard analysis (differential scanning calorimetry) on all salts used in this study revealed exotherm initiation temperature in the range of 139–199 °C and exotherm magnitude of 60–845 J/g for a single peak.
ISSN:1083-6160
1520-586X
DOI:10.1021/acs.oprd.9b00163