Oxidative Coupling of 1,3-Dicarbonyl Compounds by Cerium(IV) Ammonium Nitrate

Abstract

A fast, mild, and highly efficient method for the intermolecular coupling of 1,3-dicarbonyl compounds using cerium ammonium nitrate in CH₃CN/CH₃OH/H₂O has been described. The procedure provided a convenient method for the synthesis of 1,4-diketone derivatives with excellent yields (up to 96%) and powerful evidence for the oxidation mechanism mediated by cerium ammonium nitrate.

Keywords:

• Cerium ammonium nitrate
• coupling reaction
• 1,3-dicarbonyl compound
• radical reaction

ACKNOWLEDGMENTs

This work was supported by National Natural Science Foundation of China (Nos. 20572101 and 20672101) and Xin Miao Talent Scheme of Zhejiang (No. 2008R40G2030026).

Notes

^a Reactions performed with the 1.1 eq. of CAN in CH₃CN/CH₃OH/H₂O (2/1/1, v/v/v) at −20 °C for 15 min.

^b Isolated yield.

^c Reactions performed with the 1.1 eq. of CAN in CH₃CN/CH₃OH/H₂O (2/1/1, v/v/v) at −20 °C for 4 h.