FeTPPCl/FeCl3 Co-Catalyzed One-Pot Green Synthesis of α-Diaryl-β-alkynol Derivatives via Propargylic Carbocation Chemistry

A green and highly efficient one-pot method for alpha-diaryl-beta-alkynol derivatives in water at room temperature was developed using the cocatalysis of a Lewis acid and meso-tetraphenylporphyrin iron(III) chloride (FeTPPCl). The unprecedented transformation was promoted by a modulation of the charge properties of propargylic carbocation chemistry and the use of an in situ-generated oxonium ylide as a matching nucleophile. The reaction was performed in water at room temperature with a highly step-economic manipulation in good to excellent yields and with a broad substrate scope. Water also acts as the third reactant for the one-pot transformation. Notably, the FeTPPCl catalyst can be directly reused four times with a slight discount in yields.

Automated summary

A green and highly efficient one-pot method for the synthesis of alpha-diaryl-beta-alkynol derivatives in water at room temperature was developed using the cocatalysis of a Lewis acid and meso-tetraphenylporphyrin iron(III) chloride (FeTPPCl). Water also acts as the third reactant for the one-pot transformation, which showed good to excellent yields and a broad substrate scope. The FeTPPCl catalyst can be directly reused four times with a slight discount in yields.