Baeyer-Villiger Oxidation
The Baeyer-Villiger oxidation is the transformation of ketones into esters and cyclic ketones into lactones by the use of peroxyacids.
General features:
1. The reaction tolerates the presence of many functional groups in the ketone. 2. The regiochemistry depends on the migratory capacity of the alkyl groups, the more branched group migrates faster. 3. A wide range of peroxyacids can be used being mCPBA the most common.
Baeyer-Villiger Oxidation
Reaction Mechanism
1. The peroxyacid protonates the oxygen of the ketone. 2. The peroxyacid attacks the more electrophile carbonyl carbon. 3. Formation of the “Criegee intermediate.” 4. One of the substituents from the ketone migrates to the oxygen of the peroxide group. 5. Deprotonation leads to the ester.
Experimental Procedure
To a stirred ice-cold solution of the ketone (2.50 mmol, 1.0 eq) and m-CPBA (2.6 eq) in dry CH2Cl2 (25 mL) was added TFA (1.0 eq). The resulting mixture was stirred at room temperature for 12 h. After that time, the reaction was quenched by addition of saturated aqueous NaHCO3, and extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and evaporated to dryness. The resulting material was used in the next step without further purification.
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