Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2017 Jan 27:8:14227.
doi: 10.1038/ncomms14227.

A redox-neutral catechol synthesis

Qian Wu  1 , Dingyuan Yan  2 , Ying Chen  1 , Ting Wang  3 , Feng Xiong  2 , Wei Wei  2 , Yi Lu  2 , Wei-Yin Sun  2 , Jie Jack Li  4 , Jing Zhao  1   2
Affiliations

A redox-neutral catechol synthesis

Qian Wu et al. Nat Commun. .

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.

PubMed Disclaimer

Conflict of interest statement

The authors declare no competing financial interests.

Figures

Figure 1
Figure 1. A new approach to catechol synthesis inspired by Fischer indole synthesis.
(a) Important catechols in biology and medicine. (b) Previous work on catechol synthesis. (c) Our design inspired by Fischer indole synthesis.
Figure 2
Figure 2. Mechanistic study.
(a) Isotope labelling experiments. (b) Synthesis of 18O-labelled catechols. (c) Seeking the active intermediate. (d) The importance of the N–H bond in the substrates.
Figure 3
Figure 3. HRMS contrast of O18-labelled and non-O18-labelled substrate and product.
(a) HRMS of O18-labelled substrate and product. (b) HRMS of non-O18-labelled substrate and product.
Figure 4
Figure 4. Proposed mechanism.
A plausible mechanism illustrating how catechols are formed in acidic condition (left) and phenols are formed in alkaline condition (right).
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

See all "Cited by" articles

References

    1. Tyman J. H. Synthetic and Natural Phenols Vol. 52, Elsevier (1996).
    1. Mogwitz S., Buse J., Ehrlich S. & Roessner V. Clinical pharmacology of dopamine-modulating agents in Tourette's syndrome. Int. Rev. Neurobiol. 112, 281–349 (2013). - PubMed
    1. Ho K. Y. et al.. Effects of sex and age on the 24-h profile of growth hormone secretion in man: Importance of endogenous estradiol concentrations*. J. Clin. Endocr. Metab. 64, 51–58 (1987). - PubMed
    1. Voges H. et al.. Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCN, New York, USA (2000).
    1. Haggin J. Chemists seek greater recognition for catalysis. Chem. Eng. News 71, 23–27 (1993).

Publication types

LinkOut - more resources