Synthesis of Diarylmethanes Bearing CF 3 ‐ and CN‐Substituted All‐carbon Quaternary Centers and Diarylmalononitriles through Cyanation of δ‐Disubstituted Para ‐Quinone Methides

• Published in: European journal of organic chemistry Vol. 2021; no. 11; pp. 1643 - 1646
• Main Authors: Pan, Xiaoguang, Cao, Min, Li, Song, Wang, Hengshan, Liu, Xigong, Liu, Lei
• Format: Journal Article
• Language: English
• Published: 19.03.2021
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.202100095

Abstract 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.