4.8 Article

Intramolecular electron transfer initiated cation and radical formation through carbon-carbon bond activation

Journal

ORGANIC LETTERS
Volume 9, Issue 12, Pages 2389-2392

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol070850k

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Funding

  1. NIGMS NIH HHS [GM-62924] Funding Source: Medline

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Radical cations can be formed in a spatially and temporally controlled manner by appending a sacrificial photooxidant to an easily oxidized substrate, leading to intramolecular electron transfer upon irradiation. The anthraquinone carboxyl group is an effective photooxidant that can promote single electron oxidation from an appended arene. The resulting intermediates undergo a cleavage reaction through carbon-carbon bond activation to provide either cations or radicals that react to form a range of products.

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