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

SUBMITTER: Wu Q

PROVIDER: S-EPMC5290158 | biostudies-literature | 2017 Jan

REPOSITORIES: biostudies-literature

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A redox-neutral catechol synthesis.

Wu Qian Q Yan Dingyuan D Chen Ying Y Wang Ting T Xiong Feng F Wei Wei W Lu Yi Y Sun Wei-Yin WY Li Jie Jack JJ Zhao Jing J

Nature communications 20170127

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 ...[more]

PMID: 28128196

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