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Click. Coordinate. Catalyze. Using CuAAC Click Ligands in Small‐Molecule Model Chemistry of Tyrosinase
Author(s) -
Herzigkeit Benjamin,
Flöser Benedikt M.,
Meißner Nadja E.,
Engesser Tobias A.,
Tuczek Felix
Publication year - 2018
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201801606
Subject(s) - tyrosinase , click chemistry , cycloaddition , chemistry , hydroxylation , triazole , combinatorial chemistry , catalysis , azide , stereochemistry , enzyme , organic chemistry
Three triazolylmethylpyridine ligands are synthesized using the copper‐catalyzed azide‐alkyne cycloaddition (CuAAC). The corresponding copper(I) complexes are investigated as catalysts for the oxygenation of several monophenols, in analogy to the enzyme tyrosinase. Importantly, they show a higher catalytic activity than previously investigated systems. This is ascribed to the lower charge donation of the electron‐poor triazole heterocycle, supporting the hydroxylation of phenolic substrates by an electrophilic substitution mechanism.