Site-specific Umpolung amidation of carboxylic acids via triplet synergistic catalysis
| Autor: | Muzi Li, Jin Xie, Yunyun Ning, Shuaishuai Wang, Jie Han, Chengjian Zhu |
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| Rok vydání: | 2021 |
| Předmět: |
Multidisciplinary
010405 organic chemistry Science General Physics and Astronomy Photoredox catalysis Regioselectivity Synthetic chemistry methodology General Chemistry 010402 general chemistry 01 natural sciences Combinatorial chemistry Article General Biochemistry Genetics and Molecular Biology 0104 chemical sciences Umpolung Catalysis chemistry.chemical_compound chemistry Nucleophile Amide Functional group Synergistic catalysis Photocatalysis |
| Zdroj: | Nature Communications Nature Communications, Vol 12, Iss 1, Pp 1-9 (2021) |
| ISSN: | 2041-1723 |
| DOI: | 10.1038/s41467-021-24908-w |
| Popis: | Development of catalytic amide bond-forming methods is important because they could potentially address the existing limitations of classical methods using superstoichiometric activating reagents. In this paper, we disclose an Umpolung amidation reaction of carboxylic acids with nitroarenes and nitroalkanes enabled by the triplet synergistic catalysis of FeI2, P(V)/P(III) and photoredox catalysis, which avoids the production of byproducts from stoichiometric coupling reagents. A wide range of carboxylic acids, including aliphatic, aromatic and alkenyl acids participate smoothly in such reactions, generating structurally diverse amides in good yields (86 examples, up to 97% yield). This Umpolung amidation strategy opens a method to address challenging regioselectivity issues between nucleophilic functional groups, and complements the functional group compatibility of the classical amidation protocols. The synthetic robustness of the reaction is demonstrated by late-stage modification of complex molecules and gram-scale applications. Catalytic amide bond-forming methods is important because they could potentially address the existing limitations of classical methods using superstoichiometric activating reagents. Here the authors show an Umpolung amidation reaction of carboxylic acids with nitroarenes and nitroalkanes enabled by FeI2, P(V)/P(III) and photoredox catalysis that avoids the production of byproducts. |
| Databáze: | OpenAIRE |
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