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

Sreenivas, Kukkamudi and Khan, Faiz Ahmed (2019) FeCl3 catalyzed 1,6-conjugate addition of phenol C-nucleophiles: Facile synthesis of diarylmethanes. Tetrahedron. 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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IITH Creators:	IITH Creators ORCiD Khan, Faiz Ahmed UNSPECIFIED
Item Type:	Article
Subjects:	Chemistry
Divisions:	Department of Chemistry
Depositing User:	Team Library
Date Deposited:	23 Dec 2019 05:05
Last Modified:	23 Dec 2019 05:05
URI:	http://raiith.iith.ac.in/id/eprint/7218
Publisher URL:	http://doi.org/10.1016/j.tet.2019.130885
Related URLs:	Google Scholar

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