Mild and Rapid Method for the Generation of ortho-(Naphtho)quinone Methide Intermediates

A new mild method has been devised for generating o-(naphtho)quinone methides via fluoride-induced desilylation of silyl derivatives of o-hydroxybenzyl(or 1-naphthylmethyl) nitrate. The reactive o-(naphtho)quinone methide intermediates were trapped by C, O, N, and S nucleophiles and underwent inverse electron-demand hetero-Diels-Alder reaction with dienophiles to give stable adducts. The method has useful potential application in natural product synthesis and drug research.