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)

Full text not available from this repository. (Request a copy)

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.

[error in script]
IITH Creators:
IITH CreatorsORCiD
Khan, Faiz AhmedUNSPECIFIED
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:

Actions (login required)

View Item View Item
Statistics for RAIITH ePrint 7218 Statistics for this ePrint Item