Nickel-catalysed Suzuki-Miyaura coupling of amides
| Autor: | Emma L. Baker, Neil K. Garg, Nicholas A. Weires |
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| Rok vydání: | 2015 |
| Předmět: |
General Chemical Engineering
chemistry.chemical_element 010402 general chemistry 01 natural sciences Catalysis Metal chemistry.chemical_compound Nickel Amide Molecule Organic chemistry Molecular Structure Oxidative Coupling 010405 organic chemistry Synthon General Chemistry Ketones Combinatorial chemistry Amides 0104 chemical sciences chemistry visual_art visual_art.visual_art_medium Oxidative coupling of methane Palladium |
| Zdroj: | Nature chemistry. 8(1) |
| ISSN: | 1755-4349 |
| Popis: | The Suzuki-Miyaura coupling has become one of the most important and prevalent methods for the construction of C-C bonds. Although palladium catalysis has historically dominated the field, the use of nickel catalysis has become increasingly widespread because of its unique ability to cleave carbon-heteroatom bonds that are unreactive towards other transition metals. We report the first nickel-catalysed Suzuki-Miyaura coupling of amides, which proceeds by an uncommon cleavage of the amide C-N bond after N-tert-butoxycarbonyl activation. The methodology is mild, functional-group tolerant and can be strategically employed in sequential transition-metal-catalysed cross-coupling sequences to unite heterocyclic fragments. These studies demonstrate that amides, despite classically considered inert substrates, can be harnessed as synthons for use in reactions that form C-C bonds through cleavage of the C-N bond using non-precious metal catalysis. |
| Databáze: | OpenAIRE |
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