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. 2014 Jan 22;136(3):834-7.
doi: 10.1021/ja410538w. Epub 2013 Dec 12.

Straightforward assembly of benzoxepines by means of a rhodium(III)-catalyzed C-H functionalization of o-vinylphenols

Andrés Seoane  1 , Noelia Casanova, Noelia Quiñones, José L Mascareñas, Moisés Gulías
Affiliations

Straightforward assembly of benzoxepines by means of a rhodium(III)-catalyzed C-H functionalization of o-vinylphenols

Andrés Seoane et al. J Am Chem Soc. .

Abstract

Readily available o-vinylphenols undergo a formal (5 + 2) cycloaddition to alkynes when treated with catalytic amounts of [Cp*RhCl2]2 and Cu(OAc)2. The reaction, which involves the cleavage of the terminal C-H bond of the alkenyl moiety, generates highly valuable benzoxepine skeletons in a practical, versatile, and atom-economical manner. Using carbon monoxide instead of an alkyne as reaction partner leads to coumarin products which formally result from a (5 + 1) cycloaddition.

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