A Selective Single Step Amidation of Polyfluoroarenes
•Novel method allows for selective polyfluoroarylation of amides in a single step.•Good yields and mild reaction conditions. This chemistry establishes a method for the synthesis of per- and poly-fluoroaryl acid amides, utilizing nucleophilic aromatic substitution. Traditionally, such amides are con...
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| Veröffentlicht in: | Journal of fluorine chemistry 2021-08, Vol.248, p.109821, Article 109821 |
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| container_start_page | 109821 |
| container_title | Journal of fluorine chemistry |
| container_volume | 248 |
| creator | Noel, Alyssa M. Hamilton, Matthew Keen, Brockton Despain, Megan Day, Jon Weaver, Jimmie D. |
| description | •Novel method allows for selective polyfluoroarylation of amides in a single step.•Good yields and mild reaction conditions.
This chemistry establishes a method for the synthesis of per- and poly-fluoroaryl acid amides, utilizing nucleophilic aromatic substitution. Traditionally, such amides are constructed in a two-step process, namely, ammonolysis and then N-acylation. Herein, good yields of N-polyfluoroaryl acid amides were achieved in a single step under mild reaction conditions. Key to achieving optimal yields is the use of two equivalents of the nucleophile. In addition, the mechanism of the reaction is discussed which has implications for other related nucleophilic substitutions.
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| doi_str_mv | 10.1016/j.jfluchem.2021.109821 |
| format | Article |
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This chemistry establishes a method for the synthesis of per- and poly-fluoroaryl acid amides, utilizing nucleophilic aromatic substitution. Traditionally, such amides are constructed in a two-step process, namely, ammonolysis and then N-acylation. Herein, good yields of N-polyfluoroaryl acid amides were achieved in a single step under mild reaction conditions. Key to achieving optimal yields is the use of two equivalents of the nucleophile. In addition, the mechanism of the reaction is discussed which has implications for other related nucleophilic substitutions.
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This chemistry establishes a method for the synthesis of per- and poly-fluoroaryl acid amides, utilizing nucleophilic aromatic substitution. Traditionally, such amides are constructed in a two-step process, namely, ammonolysis and then N-acylation. Herein, good yields of N-polyfluoroaryl acid amides were achieved in a single step under mild reaction conditions. Key to achieving optimal yields is the use of two equivalents of the nucleophile. In addition, the mechanism of the reaction is discussed which has implications for other related nucleophilic substitutions.
[Display omitted]</description><subject>Acylation</subject><subject>Amide</subject><subject>Amides</subject><subject>Ammonolysis</subject><subject>and SNAr chemistry</subject><subject>Chemical synthesis</subject><subject>Fluorination</subject><subject>Organofluorines</subject><subject>Polyfluoroarylation</subject><subject>Substitution reactions</subject><issn>0022-1139</issn><issn>1873-3328</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNqFkd9L3TAUgIM49E79F6SwF196d5I2TfIiu8g2BWEDt-eQpiea0jZ3SXvB_97IVXF72dOB5Ds_P0LOKawp0OZzv-7dsNgHHNcMGM2PSjJ6QFZUiqqsKiYPyQqAsZLSSh2Tjyn1ACBAyCNyXHFgQgi-InxT3OGAdvY7LO78dD_kMOO22Iy-M7MPUxFc8TMMj7ldiMFEnDCdkg_ODAnPXuIJ-f3t66-r6_L2x_ebq81taWul5lIwwStpOVNOsLoGXstO1a2VUIvKGOaM4JY7cMC7xnXOtC3yVlLXoHG0tdUJudzX3S7tiJ3FaY5m0NvoRxMfdTBe__0z-Qd9H3ZaCs5A8Vzg4qVADH8WTLMefbI4DGbCsCTNGpaPoriSGf30D9qHJU55Pc14o2oKUjWZavaUjSGliO5tGAr62Yzu9asZ_WxG783kxPP3q7ylvarIwJc9gPmgO49RJ-txstj5mP3oLvj_9XgCSCqivg</recordid><startdate>20210801</startdate><enddate>20210801</enddate><creator>Noel, Alyssa M.</creator><creator>Hamilton, Matthew</creator><creator>Keen, Brockton</creator><creator>Despain, Megan</creator><creator>Day, Jon</creator><creator>Weaver, Jimmie D.</creator><general>Elsevier B.V</general><general>Elsevier BV</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QF</scope><scope>7QO</scope><scope>7QP</scope><scope>7QQ</scope><scope>7SC</scope><scope>7SE</scope><scope>7SP</scope><scope>7SR</scope><scope>7TA</scope><scope>7TB</scope><scope>7U5</scope><scope>7U7</scope><scope>8BQ</scope><scope>8FD</scope><scope>C1K</scope><scope>F28</scope><scope>FR3</scope><scope>H8D</scope><scope>H8G</scope><scope>JG9</scope><scope>JQ2</scope><scope>KR7</scope><scope>L7M</scope><scope>L~C</scope><scope>L~D</scope><scope>P64</scope><scope>7X8</scope><scope>5PM</scope></search><sort><creationdate>20210801</creationdate><title>A Selective Single Step Amidation of Polyfluoroarenes</title><author>Noel, Alyssa M. ; 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This chemistry establishes a method for the synthesis of per- and poly-fluoroaryl acid amides, utilizing nucleophilic aromatic substitution. Traditionally, such amides are constructed in a two-step process, namely, ammonolysis and then N-acylation. Herein, good yields of N-polyfluoroaryl acid amides were achieved in a single step under mild reaction conditions. Key to achieving optimal yields is the use of two equivalents of the nucleophile. In addition, the mechanism of the reaction is discussed which has implications for other related nucleophilic substitutions.
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| identifier | ISSN: 0022-1139 |
| ispartof | Journal of fluorine chemistry, 2021-08, Vol.248, p.109821, Article 109821 |
| issn | 0022-1139 1873-3328 |
| language | eng |
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| source | Elsevier ScienceDirect Journals Complete - AutoHoldings |
| subjects | Acylation Amide Amides Ammonolysis and SNAr chemistry Chemical synthesis Fluorination Organofluorines Polyfluoroarylation Substitution reactions |
| title | A Selective Single Step Amidation of Polyfluoroarenes |
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