A redox-neutral catechol synthesis

Qian Wu, Dingyuan Yan, Ying Chen, Ting Wang, Feng Xiong, Wei Wei, Yi Lu, Wei-Yin Sun, Jie Jack Li and Jing Zhao ()
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Qian Wu: Guangdong Key Lab of Nano-Micro Material Research, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School
Dingyuan Yan: State Key Laboratory of Coordination Chemistry, Institute of Chemistry and BioMedical Sciences, School of Chemistry and Chemical Engineering, Collaborative Innovation Centre of Chemistry for Life Sciences, Nanjing University
Ying Chen: Guangdong Key Lab of Nano-Micro Material Research, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School
Ting Wang: School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School
Feng Xiong: State Key Laboratory of Coordination Chemistry, Institute of Chemistry and BioMedical Sciences, School of Chemistry and Chemical Engineering, Collaborative Innovation Centre of Chemistry for Life Sciences, Nanjing University
Wei Wei: State Key Laboratory of Coordination Chemistry, Institute of Chemistry and BioMedical Sciences, School of Chemistry and Chemical Engineering, Collaborative Innovation Centre of Chemistry for Life Sciences, Nanjing University
Yi Lu: State Key Laboratory of Coordination Chemistry, Institute of Chemistry and BioMedical Sciences, School of Chemistry and Chemical Engineering, Collaborative Innovation Centre of Chemistry for Life Sciences, Nanjing University
Wei-Yin Sun: State Key Laboratory of Coordination Chemistry, Institute of Chemistry and BioMedical Sciences, School of Chemistry and Chemical Engineering, Collaborative Innovation Centre of Chemistry for Life Sciences, Nanjing University
Jie Jack Li: University of San Francisco
Jing Zhao: Guangdong Key Lab of Nano-Micro Material Research, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School

Nature Communications, 2017, vol. 8, issue 1, 1-9

Abstract: 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 to 18O-labelled catechols using 18O-labelled acetic acid.

Date: 2017
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DOI: 10.1038/ncomms14227

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