Toward a Visible Light Mediated Photocyclization: Cu-Based Sensitizers for the Synthesis of [5]Helicene

A photochemical synthesis of [5]helicene employing a copper-based sensitizer 7 has been developed that avoids the disadvantages associated with the traditional UV light mediated method. The visible light mediated synthesis uses common glassware and a simple household light bulb without the competing...

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Bibliographic Details
Published in:Organic letters 2012-06, Vol.14 (12), p.2988-2991
Main Authors: Hernandez-Perez, Augusto C, Vlassova, Anna, Collins, Shawn K
Format: Article
Language:English
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Summary:A photochemical synthesis of [5]helicene employing a copper-based sensitizer 7 has been developed that avoids the disadvantages associated with the traditional UV light mediated method. The visible light mediated synthesis uses common glassware and a simple household light bulb without the competing formation of [2 + 2] cycloadducts, regioisomers, or the overoxidation product benzo[ghi]perylene 3. Preliminary results show that the reaction time can be significantly reduced through the use of a continuous flow strategy.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol300983b