A Lewis acid-promoted Pinner reaction
Carbonitriles and alcohols react in a Lewis acid-promoted Pinner reaction to carboxylic esters. Best results are obtained with two equivalents of trimethylsilyl triflate as Lewis acid. Good yields are achieved with primary alcohols and aliphatic or benzylic carbonitriles, but the straightforward syn...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2013-08-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.9.179 |
| _version_ | 1818913571038298112 |
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| author | Dominik Pfaff Gregor Nemecek Joachim Podlech |
| author_facet | Dominik Pfaff Gregor Nemecek Joachim Podlech |
| author_sort | Dominik Pfaff |
| collection | DOAJ |
| description | Carbonitriles and alcohols react in a Lewis acid-promoted Pinner reaction to carboxylic esters. Best results are obtained with two equivalents of trimethylsilyl triflate as Lewis acid. Good yields are achieved with primary alcohols and aliphatic or benzylic carbonitriles, but the straightforward synthesis of acrylates and benzoates starting with acrylonitrile and benzonitrile, respectively, is similarly possible. Phenols are not acylated under these reaction conditions. The method has been used for the first total synthesis of the natural product monaspilosin. In the reaction of benzyl alcohols variable amounts of amides are formed in a Ritter-type side reaction. |
| first_indexed | 2024-12-19T23:32:36Z |
| format | Article |
| id | doaj.art-e72f09eaf2ca4d6aa1645cedfc52e305 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-19T23:32:36Z |
| publishDate | 2013-08-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-e72f09eaf2ca4d6aa1645cedfc52e3052022-12-21T20:01:41ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972013-08-01911572157710.3762/bjoc.9.1791860-5397-9-179A Lewis acid-promoted Pinner reactionDominik Pfaff0Gregor Nemecek1Joachim Podlech2Institut für Organische Chemie, Karlsruher Institut für Technologie (KIT), Fritz-Haber-Weg 6, 76131 Karlsruhe, GermanyInstitut für Organische Chemie, Karlsruher Institut für Technologie (KIT), Fritz-Haber-Weg 6, 76131 Karlsruhe, GermanyInstitut für Organische Chemie, Karlsruher Institut für Technologie (KIT), Fritz-Haber-Weg 6, 76131 Karlsruhe, GermanyCarbonitriles and alcohols react in a Lewis acid-promoted Pinner reaction to carboxylic esters. Best results are obtained with two equivalents of trimethylsilyl triflate as Lewis acid. Good yields are achieved with primary alcohols and aliphatic or benzylic carbonitriles, but the straightforward synthesis of acrylates and benzoates starting with acrylonitrile and benzonitrile, respectively, is similarly possible. Phenols are not acylated under these reaction conditions. The method has been used for the first total synthesis of the natural product monaspilosin. In the reaction of benzyl alcohols variable amounts of amides are formed in a Ritter-type side reaction.https://doi.org/10.3762/bjoc.9.179carbonitrilescarboxylic estersLewis acidsPinner reactionRitter reaction |
| spellingShingle | Dominik Pfaff Gregor Nemecek Joachim Podlech A Lewis acid-promoted Pinner reaction Beilstein Journal of Organic Chemistry carbonitriles carboxylic esters Lewis acids Pinner reaction Ritter reaction |
| title | A Lewis acid-promoted Pinner reaction |
| title_full | A Lewis acid-promoted Pinner reaction |
| title_fullStr | A Lewis acid-promoted Pinner reaction |
| title_full_unstemmed | A Lewis acid-promoted Pinner reaction |
| title_short | A Lewis acid-promoted Pinner reaction |
| title_sort | lewis acid promoted pinner reaction |
| topic | carbonitriles carboxylic esters Lewis acids Pinner reaction Ritter reaction |
| url | https://doi.org/10.3762/bjoc.9.179 |
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