1,1,1,3,3,3-Hexafluoro-2-propanol (HFIP)-promoted regiospecific 1,6-hydroarylation of para-quinone methides with N-heteroarenes: Synthesis of unsymmetrical triarylmethanes.

In this work, a recyclable and highly regioselective 1,6-hydroarylation of para -quinone methides (p -QMs) with N -heteroarenes has been developed under mild conditions. 1,1,1,3,3,3-Hexafluoro-2-propanol (HFIP) as a solvent plays a significant role in this transformation to achieve a wide assortment of unsymmetrical triarylmethanes with high yields and excellent regioselectivity. This novel reaction is featured a very broad substrate scope and outstanding functional group tolerance and could also be scaled-up. Moreover, this Friedel-Crafts alkylation pathway is further supported by replacing HFIP with trifluoroethanol (TFE) in the control reactions. A highly regioselective 1,6-hydroarylation of para -quinone methides (p -QMs) with N -heteroarenes has been developed under mild conditions. 1,1,1,3,3,3-Hexafluoro-2-propanol (HFIP) as a solvent plays a significant role in this transformation to achieve a wide assortment of unsymmetrical triarylmethanes with high yields and excellent regioselectivity. Moreover, this transformation can be easily extended to a gram scale-synthesis level. [Display omitted] [ABSTRACT FROM AUTHOR]