Propargyl alpha-aryl-alpha-diazoacetates as robust reagents for the effective C-H bond functionalization of 1,3-diketones via scandium catalysis

Abstract

Propargyl α-aryl-α-diazoacetate a new class of reagent is developed for the effective CH bond functionalization of 1,3-diketones at room temperature. The combination of scandium triflate and propargyl α-aryl-α-diazoacetate proved to be efficient catalyst-reagent system for the controlled CH bond functionalization to afford 1,3-dicarbonyl alkylation. Propargyl α-aryl-α-diazoacetate a new class of reagent is developed for the effective CH bond functionalization of 1,3-diketones at room temperature. The combination of scandium triflate and propargyl α-aryl-α-diazoacetate proved to be efficient catalyst-reagent system for the controlled CH bond functionalization to afford 1,3-dicarbonyl alkylation. The protocol uses inexpensive Sc(OTf)3 (5 mol%) and the reaction did not require the use of expensive catalysts or ligands and worked efficiently at room temperature. The practicality of the protocol has been demonstrated by the gram scale synthesis.