4.8 Article

[3+2] Cycloadditions of Aryl Cyclopropyl Ketones by Visible Light Photocatalysis

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 5, Pages 1162-1164

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja107849y

Keywords

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Funding

  1. ACS PRF [49817-ND1]
  2. NIH [GM095666, RR08389-01]
  3. Sloan Foundation
  4. Beckman Foundation
  5. Research Corporation
  6. NSF [CHE-9208463, CHE-9629688]

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We report a new method for the formal [3+2] reaction of aryl cyclopropyl ketones with olefins to generate highly substituted cyclopentane ring systems. The key initiation step in this process is the one-electron reduction of the ketone to the corresponding radical anion, which is accomplished using a photocatalytic system comprising Ru(bpy)(3)(2+), La(OTf)(3), and TMEDA.

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