Rapid C-H Transformation: Addition of Diarylmethanes to Imines in Seconds by Catalytic Use of Base

The addition of diarylmethanes or methylarenes via activation of benzylic C(sp³)-H bonds to N-aryl imines proceeds under catalysis by alkali hexamethyldisilazide (HMDS) base to give N-(1,2,2-triarylethyl)anilines or N-(1,2-diarylethyl)anilines, respectively. In the presence of 10 mol % of LiHMDS at room temperature, the diarylmethane addition equilibrates within 20-30 s and is driven to near completion by cooling the reaction mixture to −25 °C, providing N-(1,2,2-triarylethyl)aniline in a >90% yield.