A dual biomimetic process for the selective aerobic oxidative coupling of primary amines using pyrogallol as a precatalyst. Isolation of the [5 + 2] cycloaddition redox intermediates
| Autor: | M.B. Fleury, Karim Hammad, Martine Largeron, Patrick Deschamps |
|---|---|
| Přispěvatelé: | Cibles Thérapeutiques et conception de médicaments (CiTCoM - UMR 8038), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Paris (UP), Université Paris Descartes - Paris 5 (UPD5)-Centre National de la Recherche Scientifique (CNRS) |
| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
amines
010402 general chemistry 01 natural sciences Redox chemistry.chemical_compound Cascade reaction [CHIM.CRIS]Chemical Sciences/Cristallography biomimetic oxidation [CHIM]Chemical Sciences Environmental Chemistry organocatalysis pyrogallol second order biomimicry ComputingMilieux_MISCELLANEOUS benzimidazoles Primary (chemistry) purpurogallin biosynthesis 010405 organic chemistry [CHIM.ORGA]Chemical Sciences/Organic chemistry [CHIM.CATA]Chemical Sciences/Catalysis Pollution Combinatorial chemistry copper amine oxidases Cycloaddition 0104 chemical sciences Pyrogallol chemistry imines precatalyst Amine gas treating Oxidative coupling of methane cascade reaction Purpurogallin |
| Zdroj: | Green Chemistry Green Chemistry, Royal Society of Chemistry, 2020, 22 (6), pp.1894-1905. ⟨10.1039/c9gc03992a⟩ Green Chemistry, Royal Society of Chemistry, 2020, ⟨10.1039/c9gc03992a⟩ |
| ISSN: | 1463-9262 1463-9270 |
| DOI: | 10.1039/c9gc03992a⟩ |
| Popis: | International audience; A bioinspired organocatalytic cascade reaction mimicking both purpurogallin biosynthesis and copper amine oxidases (CuAOs) activity is described, at room temperature under ambient air, for the activation of the α-C–H bond of primary amines. The reaction sequence uses low-cost commercially available pyrogallol as a precatalyst which undergoes an in situ oxidative self-processing step, resulting in its conversion into natural purpurogallin, a [5 + 2] cycloaddition redox intermediate. This is further involved in the CuAOs-like transamination mechanism for producing, under single turnover, the active biomimetic organocatalyst which mediates the selective oxidative coupling of primary amines, including the non-activated substrates of CuAOs. Without any metal cocatalyst or additives, the protocol gives access to cross-coupled imines as well as 1,2-disubstituted benzimidazoles. The isolation of not easily accessible [5 + 2] cycloaddition redox intermediates provides direct and clear evidence for the proposed dual biomimetic process. |
| Databáze: | OpenAIRE |
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