Metal-Free Transamidation of Secondary Amides via Selective N-C Cleavage under Mild Conditions
Nonplanar, electronically destabilized amides have emerged as powerful intermediates in organic synthesis. We report a highly selective method for transamidation of common secondary amides under mild, metal-free conditions that relies on transient N-selective functionalization to weaken amidic reson...
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| Vydáno v: | Organic letters Ročník 19; číslo 7; s. 1614 |
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| Hlavní autoři: | , , , , |
| Médium: | Journal Article |
| Jazyk: | angličtina |
| Vydáno: |
United States
07.04.2017
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| ISSN: | 1523-7052, 1523-7052 |
| On-line přístup: | Zjistit podrobnosti o přístupu |
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| Shrnutí: | Nonplanar, electronically destabilized amides have emerged as powerful intermediates in organic synthesis. We report a highly selective method for transamidation of common secondary amides under mild, metal-free conditions that relies on transient N-selective functionalization to weaken amidic resonance. The combination of rational modification of the amide bond with nucleophilic addition mechanism, and the thermodynamic collapse of the resultant tetrahedral intermediate constitutes a two-step procedure to accomplish a challenging transamidation of secondary amides under mild conditions. |
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| Bibliografie: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
| ISSN: | 1523-7052 1523-7052 |
| DOI: | 10.1021/acs.orglett.7b00429 |