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Synthesis 2009(9): 1499-1505
DOI: 10.1055/s-0028-1088165
DOI: 10.1055/s-0028-1088165
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Higher Helicenes via Olefin Metathesis and C-H Activation
Further Information
Publication History
Received
27 October 2008
Publication Date:
25 March 2009 (online)
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Abstract
Functionalized heterohelicenes were prepared using sequential olefin metathesis and direct arylation reactions. Functionalization via C-H activation always occurs at the least hindered position of the [5]helicene carbon skeleton. Attempts at blocking the least hindered positions to force arylation at the interior of the helicene skeleton result in decomposition of the starting material. Installation of larger aromatic groups via arylation can form helicenes albeit with limited solubility in common organic solvents.
Key words
helicene - olefin metathesis - C-H activation - heterohelicene - arylation