Thermodynamically Favorable Synthesis of 2-Oxazolidinones through Silver-Catalyzed Reaction of Propargylic Alcohols, CO2, and 2-Aminoethanols

Development of catalytic routes to incorporate CO2 into carbonyl compounds at mild conditions remains attractive and challenging. Herein, a one‐pot three‐component cascade reaction of terminal propargylic alcohols, CO2, and 2‐aminoethanols through AgI‐based catalysis is reported for the synthesis of carbonyl compounds through C−O/C−N bond formation. This thermodynamically favorable route can be ingeniously regulated to afford a wide range of 2‐oxazolidinones along with concurrent production of α‐hydroxyl ketone derivatives in excellent yields and selectivity. Preliminary mechanistic studies indicate that such a process proceeds through successive formation of α‐alkylidene cyclic carbonate, β‐oxopropylcarbamate, and 2‐oxazolidinones. Three in a pot: A thermodynamically feasible pathway for CO2 conversion is successfully performed to concurrently synthesize 2‐oxazolidinones and α‐hydroxyl ketones through a three‐component reaction of propargylic alcohols, CO2, and 2‐aminoalcohols. As a consequence, the thermodynamic limitation for the condensation reaction of 2‐aminoalcohols and CO2 is circumvented by avoiding the dehydration step.