4.7 Article

Fast and high-efficiency synthesis of 2-substituted benzothiazoles via combining enzyme catalysis and photoredox catalysis in one-pot

Journal

BIOORGANIC CHEMISTRY
Volume 107, Issue -, Pages -

Publisher

ACADEMIC PRESS INC ELSEVIER SCIENCE
DOI: 10.1016/j.bioorg.2020.104607

Keywords

Eco-friendly; Photocatalytic reaction; Visible-light; Benzothiazoles; One-pot synthesis

Funding

  1. National Key R&D Program of China [2018YFA0901600]
  2. Comprehensive Training Platform of Specialized Laboratory, College of Chemistry, Sichuan University

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By combining enzymatic and visible-light catalysis, an efficient and green method for synthesizing 2-substituted benzothiazoles has been developed, achieving high yields in a short amount of time with nearly 100% atomic utilization. This method showcases the potential of harnessing the catalytic activity of enzymes and visible light for organic synthesis, without the need for additional oxidants or metals, making it environmentally friendly.
An efficient and green method, combining enzymatic and visible-light catalysis for synthesis of the widely applicable 2-substituted benzothiazoles, has been developed. This method features a relay catalysis protocol consisting of biocatalytic promiscuity and visible-light-induced subsequent oxidization of 2-phenyl benzothiazolines. The whole reaction process is very high-efficiency, achieving 99% yield in just 10 min, under an air atmosphere, nearly 100% atomic utilization, and the 2-substituted benzothiazole products were obtained in good to excellent yields with a wide range of substrates. This reaction is the other example of combining the nonnatural catalytic activity of hydrolases with visible-light catalysis for organic synthesis and the catalytic system does not require additional oxidants or metals, which is good for the environment.

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