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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| Published in | Organic process research & development Vol. 23; no. 6; pp. 1269 - 1274 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
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WASHINGTON
American Chemical Society
21.06.2019
Amer Chemical Soc |
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| Abstract | 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. |
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| AbstractList | 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. 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 degrees C and exotherm magnitude of 60-845 J/g for a single peak. |
| Author | Bader, Joshua Gallagher, Rory T Vickery, Thomas Seidl, Thomas L Stuart, David R Orella, Charles |
| AuthorAffiliation | Department of Chemistry Merck & Co., Inc Department of Process Research and Development ExecuPharm |
| AuthorAffiliation_xml | – name: Merck & Co., Inc – name: Department of Chemistry – name: Department of Process Research and Development – name: ExecuPharm |
| Author_xml | – sequence: 1 givenname: Rory T surname: Gallagher fullname: Gallagher, Rory T organization: Department of Chemistry – sequence: 2 givenname: Thomas L surname: Seidl fullname: Seidl, Thomas L organization: Department of Chemistry – sequence: 3 givenname: Joshua surname: Bader fullname: Bader, Joshua organization: ExecuPharm – sequence: 4 givenname: Charles surname: Orella fullname: Orella, Charles email: dstuart@pdx.edu organization: Merck & Co., Inc – sequence: 5 givenname: Thomas surname: Vickery fullname: Vickery, Thomas organization: Merck & Co., Inc – sequence: 6 givenname: David R orcidid: 0000-0003-3519-9067 surname: Stuart fullname: Stuart, David R email: charles_orella@merck.com organization: Department of Chemistry |
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| Keywords | anion exchange solid-phase diaryliodonium arylation MILD SYNTHESIS ACID ONE-POT SYNTHESIS SCOPE ARENES IODINE EXCHANGE |
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| Snippet | Herein, we describe the discovery and development of a method to exchange the counteranion component of diaryliodonium salts, which is a critical step for... |
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| SubjectTerms | Chemistry Chemistry, Applied Chemistry, Organic Physical Sciences Science & Technology |
| Title | Anion Metathesis of Diaryliodonium Tosylate Salts with a Solid-Phase Column Constructed from Readily Available Laboratory Consumables |
| URI | http://dx.doi.org/10.1021/acs.oprd.9b00163 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000473115800016 |
| Volume | 23 |
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