4.7 Article

Photocatalytic Hydroalkylation of Aryl-Alkenes

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 16, Pages 11042-11047

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c01304

Keywords

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Funding

  1. European Research Council (ERC) under the European Union?s Horizon 2020 research and innovation programme [864991]
  2. TU Wien Bibliothek
  3. European Research Council (ERC) [864991] Funding Source: European Research Council (ERC)

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This research presents a visible light-catalyzed hydroalkylation reaction of aryl-alkenes with alkyl iodides. The reaction demonstrates high yields of various hydroalkylation products, tolerating primary, secondary, and tertiary alkyl iodides. Mechanistic experiments reveal the pathway of halogen atom transfer followed by a radical-polar crossover mechanism.
Here, we present a visible light-catalyzed hydroalkylation of aryl-alkenes affording C-C bonds using aryl-alkenes and alkyl iodides. We demonstrate the formation of various hydroalkylation products in excellent yields, with primary, secondary, and tertiary alkyl iodides being tolerated in the reaction. Mechanistic experiments reveal a pathway consisting of halogen atom transfer followed by a radical-polar crossover mechanism delivering the desired hydroalkylation products.

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