A redox-neutral catechol synthesis

• Published in: Nature communications Vol. 8; no. 1; p. 14227
• Main Authors: Wu, Qian, Yan, Dingyuan, Chen, Ying, Wang, Ting, Xiong, Feng, Wei, Wei, Lu, Yi, Sun, Wei-Yin, Li, Jie Jack, Zhao, Jing
• Format: Journal Article
• Language: English
• Published: England Nature Publishing Group 27.01.2017; Nature Portfolio
• Subjects: Acetamides - chemistry; Acetic Acid - chemistry; Biology; Catalysis; Catechols - chemical synthesis; Chemistry; Dopamine; Fluorescence; Hydroxylation; Iridium - chemistry; Oxidation-Reduction; Oxygen - chemistry; Oxygen Isotopes - chemistry; Parkinson's disease; Phenols; Phenols - chemistry; Staining and Labeling - methods; China
• ISSN: 2041-1723; 2041-1723
• DOI: 10.1038/ncomms14227

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 O-labelled catechols using O-labelled acetic acid.