Domino Friedel-Crafts Cyclization for Helicene Synthesis

J. Ichikawa; M. Yokota; T. Kudo; S. Umezaki

doi:10.1055/s-2008-1078684

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000131.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synfacts 2008(9): 0936-0936
DOI: 10.1055/s-2008-1078684

Synthesis of Materials and Unnatural Products

Domino Friedel-Crafts Cyclization for Helicene Synthesis

Contributor(s): Timothy M. Swager, Jose M. Lobez
J. Ichikawa*, M. Yokota, T. Kudo, S. Umezaki
University of Tsukuba, Ibaraki and The University of Tokyo, Japan

Further Information

Publication History

Publication Date:
22 August 2008 (online)

Permissions and Reprints

Significance

The authors describe a strategy for the synthesis of helicene-type molecules based on a domino Friedel-Crafts reaction as presented above. The use of magic acid for fluorine-stabilized carbocation formation allows for the intramolecular Friedel-Crafts reaction to take place. This was studied for the model compound A. When a second aromatic system is present within the same molecule, a second Friedel-Crafts reaction can take place, yielding a helicene-type molecule after high-yielding dehydrogenation.