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Novel Synthesis of 3‑Substituted 2,3-Dihydrobenzofurans via ortho-Quinone Methide Intermediates Generated in Situ

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journal contribution
posted on 07.03.2014, 00:00 by Abdul kadar Shaikh, George Varvounis
A new method is presented for the regioselective one-pot synthesis of 3-substituted 2,3-dihydrobenzofurans from 2-bromo-1-{2-[(tri­iso­propyl­silyl)­oxy]­phenyl}­ethyl nitrate by fluoride-induced desilylation leading to o-quinone methide generation, Michael addition of different C, N, O, and S nucleophiles, and intramolecular 5-exo-tet elimination of a bromide anion. The method has potential synthetic applications in drug discovery.