Photoinduced Palladium-Catalyzed Radical Germylative Arylation of Alkenes with Chlorogermanes.

J Org Chem

College of Material, Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Key Laboratory of Organosilicon Material Technology of Zhejiang Province, Hangzhou Normal University, Hangzhou, 311121, Zhejiang, P. R. China.

Published: September 2024

AI Article Synopsis

  • - The study presents a method for creating germanium-substituted indolin-2-ones using a palladium catalyst and chlorogermanes, triggered by visible light.
  • - This process takes place under mild conditions and produces good to excellent yields, making it a convenient approach for synthesizing these compounds.
  • - A critical aspect of the method involves activating germanium-chloride bonds with a palladium complex under light, with supporting evidence for germanium radicals provided through electron paramagnetic resonance spectroscopy.

Article Abstract

We describe a visible light-induced palladium-catalyzed radical germylative arylation of alkenes with easily accessible chlorogermanes. This protocol provides expedient access to germanium-substituted indolin-2-ones in good to excellent yields under mild reaction conditions. The key step for this strategy lies in the reductive activation of germanium-chloride bonds with an excited palladium complex under visible light irradiation. The involvement of germanium radicals was evidenced by electron paramagnetic resonance spectroscopy experiments.

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http://dx.doi.org/10.1021/acs.joc.4c01456DOI Listing

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