Rapid C–H Transformation: Addition of Diarylmethanes to Imines in Seconds by Catalytic Use of Base
Christian Weindl, Sebastian L. Helmbrecht, Lukas Hintermann
Abstract
The addition of diarylmethanes or methylarenes via activation of benzylic C(sp 3 )–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.
Topics & Concepts
Base (topology)Transformation (genetics)CatalysisChemistryMathematicsOrganic chemistryBiochemistryMathematical analysisGeneCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsAsymmetric Hydrogenation and Catalysis