Palladium-Catalyzed Decarboxylative 1,2-Addition of Carboxylic Acids to Glyoxylic Acid Esters

The formation of C-C-bonds constitutes one of the most fundamental synthetic operations in organic chemistry. The nucleophilic addition of preformed organometallic reagents to an electrophilic carbonyl functionality represents a classical method for the selective construction of a C-C-bond. However, the synthesis and utilization of an organometallic reagent is associated with an unfavorable environmental profile. Herein, we disclose a Palladium-catalyzed decarboxylative 1,2-addition of carboxylic acids to glyoxylic acid esters. This novel method provides access to the mandelic acid scaffold in good yields. Easy-to-handle and readily available benzoic acids are utilized as more sustainable alternative to preformed organometallic nucleophiles.

Automated summary

This study presents a palladium-catalyzed decarboxylative 1,2-addition of carboxylic acids to glyoxylic acid esters, providing access to the mandelic acid scaffold in good yields. The method utilizes readily available benzoic acids as a more sustainable alternative to preformed organometallic nucleophiles, showing promise for environmentally friendly organic synthesis.