FeCl3 catalyzed 1,6-conjugate addition of phenol C-nucleophiles: Facile synthesis of diarylmethanes

Sreenivas, Kukkamudi and Khan, Faiz Ahmed (2020) FeCl3 catalyzed 1,6-conjugate addition of phenol C-nucleophiles: Facile synthesis of diarylmethanes. Tetrahedron, 76 (6). pp. 1-9. ISSN 0040-4020 (In Press)

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Abstract

An efficient synthesis of diarylmethane derivatives from phenol and a p-quinone methide surrogate cyclohexadienone derivative has been described. This 1,6-conjugate addition reaction is catalyzed by earth abundant FeCl3 and it proceeds via a consecutive Michael type addition followed by aromatization. Various proportions of phenol and cyclohexadienone produced exclusively mono, bis and tris addition products. Interestingly, di-tert-butylphenol gave addition product with concomitant loss of one of the tertiary butyl groups of the phenol moiety via retro-Friedel-Crafts reaction. This strategy demonstrates a straightforward access to wide range of diarylmethane derivatives possessing biologically significant ortho-methoxyphenol moiety under mild reaction conditions.

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