Guanidines strike back: Exceptional Substrate Diversity in Oxygenation Reactions Catalyzed by a Bis(µ-oxo) Copper Complex.

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ID: 99808
2020
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Ranked #22 of 117 articles by views in Chemistry (Weinheim an der Bergstrasse, Germany)

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Abstract
The enzyme tyrosinase contains a reactive side-on peroxo dicopper(II) center as catalytically active species in C-H oxygenation reactions. The tyrosinase activity of the isomeric bis(µ-oxo) dicopper(III) form has been discussed controversially. We describe the synthesis and characterization of bis(µ-oxo) dicopper(III) species [Cu 2 (µ-O) 2 ( L1 ) 2 ](X) 2 ([ O1 ](X) 2 , X = PF 6 - , BF 4 - , OTf - , ClO 4 - ) via UV/Vis, Raman and XAS spectroscopy as well as cryo-UHR-ESI mass spectrometry, stabilized by the novel hybrid guanidine ligand 2-{2-((dimethylamino)methyl)phenyl}-1,1,3,3-tetramethylguanidine ( L1 ) . We highlight selective oxygenation of a plethora of phenolic substrates mediated by [ O1 ](PF 6 ) 2 , that results in mono- and bicyclic quinones and provides an attractive strategy on the route to design new phenazines . The selectivity is predictable using the Fukui function which is hereby introduced into tyrosinase model chemistry. Our bioinspired catalysis harnesses molecular dioxygen for organic transformations and achieves a substrate diversity which goes far beyond the enzyme's scope.
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herrespawlis2020guanidineschemistry Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Sonja Herres-Pawlis, Melanie Paul, Melissa Teubner, Benjamin Grimm-Lebsanft, Christiane Golchert, Yannick Meiners, Laura Senft, Kristina Keisers, Patricia Liebhäuser, Thomas Rösener, Florian Biebl, Sören Buchenau, Maria Naumova, Vadim Murzin, Roxanne Krug, Alexander Hoffmann, Jörg Pietruszka, Ivana Ivanovic-Burmazovic, Michael Rübhausen
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Journal Chemistry (Weinheim an der Bergstrasse, Germany)
Year 2020
DOI
10.1002/chem.202000664
URL
Keywords
tyrosinase copper catalysis dioxygen activation guanidines phenazines

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