Nickel-Catalyzed Esterification of Aliphatic Amides
| Autor: | Chris H. Senanayake, Neil K. Garg, Sarah M. Anthony, Jean-Nicolas Desrosiers, Emma L. Baker, Liana Hie |
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| Rok vydání: | 2016 |
| Předmět: |
Steric effects
esterification Molecular Conformation Homogeneous catalysis 010402 general chemistry 01 natural sciences Article Catalysis Stereocenter chemistry.chemical_compound nickel Nucleophile Nickel Amide Organometallic Compounds cross-coupling Organic chemistry Bond cleavage 010405 organic chemistry Organic Chemistry Esters General Chemistry General Medicine Amides homogeneous catalysis aliphatic amides 0104 chemical sciences chemistry Chemical Sciences Selectivity |
| Zdroj: | Angewandte Chemie (International ed. in English), vol 55, iss 48 |
| Popis: | Recent studies have demonstrated that amides can be used in nickel-catalyzed reactions that lead to cleavage of the amide C-N bond, with formation of a C-C or C-heteroatom bond. However, the general scope of these methodologies has been restricted to amides where the carbonyl is directly attached to an arene or heteroarene. We now report the nickel-catalyzed esterification of amides derived from aliphatic carboxylic acids. The transformation requires only a slight excess of the alcohol nucleophile and is tolerant of heterocycles, substrates with epimerizable stereocenters, and sterically congested coupling partners. Moreover, a series of amide competition experiments establish selectivity principles that will aid future synthetic design. These studies overcome a critical limitation of current Ni-catalyzed amide couplings and are expected to further stimulate the use of amides as synthetic building blocks in C-N bond cleavage processes. |
| Databáze: | OpenAIRE |
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