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Synthesis of Diarylmethanes Bearing CF 3 ‐ and CN‐Substituted All‐carbon Quaternary Centers and Diarylmalononitriles through Cyanation of δ‐Disubstituted Para ‐Quinone Methides
Author(s) -
Pan Xiaoguang,
Cao Min,
Li Song,
Wang Hengshan,
Liu Xigong,
Liu Lei
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100095
Subject(s) - cyanation , chemistry , stereocenter , moiety , quinone , aryl , quaternary carbon , combinatorial chemistry , organic chemistry , catalysis , enantioselective synthesis , alkyl
An effective construction of diarylmethanes containing CF 3 ‐ and CN‐substituted all‐carbon quaternary stereocenters via cyanation of δ‐CF 3 ‐δ‐aryl disubstituted para ‐quinone methides has been described. The reaction proceeds smoothly under simple and mild conditions and exhibits a broad scope of δ‐CF 3 ‐δ‐aryl disubstituted para ‐quinone methides in high efficiency. δ‐CF 3 ‐δ‐alkynyl‐disubstituted para ‐quinone methides also proved to be suitable substrates. The rich chemistry of the cyano moiety allows for rapid access to other valuable CF 3 ‐substituted di‐ and triarylmethanes containing all‐carbon quaternary centers that are otherwise difficult to synthesize. The generality of the method was further demonstrated by cyanation of δ‐CN‐substituted para ‐quinone methides furnishing diarylmalononitriles in good yields.