4.8 Article

Visible-Light-Mediated Metal-Free Difunctionalization of Alkenes with CO2 and Silanes or C(sp3)-H Alkanes

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 52, Pages 17220-17224

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201811266

Keywords

alkene difunctionalization; carbon dioxide; C-H activation; photocatalysis; Si-H functionalization

Funding

  1. National University of Singapore
  2. Ministry of Education (MOE) of Singapore [R-143-000-645-112, R-143-000-696-114, R-143-000-A30-112]
  3. National Natural Science Foundation of China [21702142]
  4. GSK-EDB [R-143-000-687-592]

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Catalytic alkene difunctionalization via Si-H and C-H activations represents an ideal atom- and step-economic pathway for quick assembly of molecular complexity. We herein developed a visible-light-promoted metal-free difunctionalization of alkenes using abundant CO2 and readily available Si-H and C(sp(3))-H bonds as feedstocks. Through the merger of photoredox and hydrogen-atom-transfer catalysis, a variety of value-added compounds, such as beta-silacarboxylic acids and acids bearing a gamma-heteroatom (e.g., N, O, S) could be directly accessed from simple alkenes in a redox-neutral fashion.

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