Synthesis of Diarylmethanes Bearing CF3- and CN-Substituted All-carbon Quaternary Centers and Diarylmalononitriles through Cyanation of δ-Disubstituted Para-Quinone Methides

An effective construction of diarylmethanes containing CF3- and CN-substituted all-carbon quaternary stereocenters via cyanation of delta-CF3-delta-aryl disubstituted para-quinone methides has been described. The reaction proceeds smoothly under simple and mild conditions and exhibits a broad scope of delta-CF3-delta-aryl disubstituted para-quinone methides in high efficiency. delta-CF3-delta-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 CF3-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 delta-CN-substituted para-quinone methides furnishing diarylmalononitriles in good yields.

Automated summary

An efficient construction of diarylmethanes containing CF3- and CN-substituted all-carbon quaternary stereocenters has been achieved via cyanation of delta-CF3-delta-aryl disubstituted para-quinone methides. The method shows broad scope, high efficiency, and enables rapid access to valuable CF3-substituted di- and triarylmethanes. Additionally, cyanation of delta-CN-substituted para-quinone methides furnishes diarylmalononitriles in good yields, demonstrating the generality of the approach.