Intramolecular aryne-ene reaction: synthetic and mechanistic studies.

Department of Chemistry, University of Toronto, 80 Saint George Street, Toronto, Ontario M5S 3H6, Canada.
Journal of the American Chemical Society (Impact Factor: 10.68). 08/2011; 133(36):14200-3. DOI: 10.1021/ja205405n
Source: PubMed

ABSTRACT Although the chemistry of arynes is well developed, some challenges still remain. The ene reaction of arynes has not gained widespread use in synthesis as a result of poor yields and selectivity. A general, high yielding and selective intramolecular aryne-ene reaction is described providing various benzofused carbo- and heterocycles. Mechanistic data is presented, and a rationale for the resulting stereochemistry is discussed.

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