title: A redox-neutral catechol synthesis.
abstract: Ubiquitous tyrosinase catalyses the aerobic oxidation of phenols to catechols through the binuclear copper centres. Here, inspired by the Fischer indole synthesis, we report an iridium-catalysed tyrosinase-like approach to catechols, employing an oxyacetamide-directed C-H hydroxylation on phenols. This method achieves one-step, redox-neutral synthesis of catechols with diverse substituent groups under mild conditions. Mechanistic studies confirm that the directing group (DG) oxyacetamide acts as the oxygen source. This strategy has been applied to the synthesis of different important catechols with fluorescent property and bioactivity from the corresponding phenols. Finally, our method also provides a convenient route to18O-labelled catechols using18O-labelled acetic acid.
authors.affiliation: Guangdong Key Lab of Nano-Micro Material Research, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen 518055, China.
authors.forename: Qian
authors.initials: Q
authors.lastname: Wu
authors.affiliation: State Key Laboratory of Coordination Chemistry, Department of Chemistry, Institute of Chemistry and BioMedical Sciences, School of Chemistry and Chemical Engineering, Collaborative Innovation Centre of Chemistry for Life Sciences, Nanjing University, 163 Xianlin Avenue, Nanjing 210023, China.
authors.forename: Dingyuan
authors.initials: D
authors.lastname: Yan
authors.affiliation: Guangdong Key Lab of Nano-Micro Material Research, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen 518055, China.
authors.forename: Ying
authors.initials: Y
authors.lastname: Chen
authors.affiliation: School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen 518055, China.
authors.forename: Ting
authors.initials: T
authors.lastname: Wang
authors.affiliation: State Key Laboratory of Coordination Chemistry, Department of Chemistry, Institute of Chemistry and BioMedical Sciences, School of Chemistry and Chemical Engineering, Collaborative Innovation Centre of Chemistry for Life Sciences, Nanjing University, 163 Xianlin Avenue, Nanjing 210023, China.
authors.forename: Feng
authors.initials: F
authors.lastname: Xiong
authors.affiliation: State Key Laboratory of Coordination Chemistry, Department of Chemistry, Institute of Chemistry and BioMedical Sciences, School of Chemistry and Chemical Engineering, Collaborative Innovation Centre of Chemistry for Life Sciences, Nanjing University, 163 Xianlin Avenue, Nanjing 210023, China.
authors.forename: Wei
authors.initials: W
authors.lastname: Wei
authors.affiliation: State Key Laboratory of Coordination Chemistry, Department of Chemistry, Institute of Chemistry and BioMedical Sciences, School of Chemistry and Chemical Engineering, Collaborative Innovation Centre of Chemistry for Life Sciences, Nanjing University, 163 Xianlin Avenue, Nanjing 210023, China.
authors.forename: Yi
authors.initials: Y
authors.lastname: Lu
authors.affiliation: State Key Laboratory of Coordination Chemistry, Department of Chemistry, Institute of Chemistry and BioMedical Sciences, School of Chemistry and Chemical Engineering, Collaborative Innovation Centre of Chemistry for Life Sciences, Nanjing University, 163 Xianlin Avenue, Nanjing 210023, China.
authors.forename: Wei-Yin
authors.initials: WY
authors.lastname: Sun
authors.affiliation: Department of Chemistry, University of San Francisco, 2130 Fulton Street, San Francisco, California 94117, USA.
authors.forename: Jie Jack
authors.initials: JJ
authors.lastname: Li
authors.affiliation: Guangdong Key Lab of Nano-Micro Material Research, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen 518055, China.|State Key Laboratory of Coordination Chemistry, Department of Chemistry, Institute of Chemistry and BioMedical Sciences, School of Chemistry and Chemical Engineering, Collaborative Innovation Centre of Chemistry for Life Sciences, Nanjing University, 163 Xianlin Avenue, Nanjing 210023, China.
authors.forename: Jing
authors.identifier: 0000-0001-5177-5699
authors.initials: J
authors.lastname: Zhao
mesh_terms: D000081:Acetamides / Q000737:chemistry; D019342:Acetic Acid / Q000737:chemistry; D002384:Catalysis; D002396:Catechols / Q000138:chemical synthesis*; D005453:Fluorescence; D006900:Hydroxylation; D007495:Iridium / Q000737:chemistry*; D010084:Oxidation-Reduction; D010100:Oxygen / Q000737:chemistry*; D010103:Oxygen Isotopes / Q000737:chemistry; D010636:Phenols / Q000737:chemistry*; D013194:Staining and Labeling / Q000379:methods
chemical_list: D000081:Acetamides; D002396:Catechols; D010103:Oxygen Isotopes; C000615259:Oxygen-18; D010636:Phenols; D007495:Iridium; D019342:Acetic Acid; D010100:Oxygen