Acid-Catalyzed Regioselective Synthesis of α-Diarylmethyl Substituted Phenols and para-Quinone Methides in Water

A facile and efficient method for the synthesis of alpha-diarylmethyl substituted phenols from para-quinone methides (p-QMs) with phenols has been developed by using phosphoric acid as the catalyst and water as the green solvent under mild conditions. In addition, when TEMPO was added as an additive for the reaction, the diaryl-substituted para-quinone methides could be generated as the target product. The reactions show high functional group tolerance, good to excellent yields and unique selectivity, and a broad range of alpha-diarylmethyl motif containing phenol(s) and quinones could be prepared through the divergent methods. Furthermore, a series of control experiments were performed to gain the insights of the plausible mechanisms. These protocols have a high atomic economy, and may have significant implications for the construction of C(sp(3))-C(sp(2)) bonds in organic synthesis.

Automated summary

A facile and efficient method for the synthesis of alpha-diarylmethyl substituted phenols has been developed using phosphoric acid as the catalyst and water as the green solvent. Addition of TEMPO as an additive allows for the generation of diaryl-substituted para-quinone methides. These reactions exhibit high functional group tolerance, good to excellent yields, and unique selectivity, providing a new method for organic synthesis.