Rate Enhancement in CAN-Promoted Pd(PPh3)2Cl2‑Catalyzed Oxidative Cyclization:
Synthesis of 2‑Ketofuran-4-carboxylate Esters
Posted on 2019-02-28 - 14:49
Stoichiometric
ceric ammonium nitrate (CAN) and a catalytic amount
of Pd(PPh3)2Cl2 (5 mol %) can rapidly
produce multisubstituted 2-ketofuran-4-carboxylate esters from 2-propargylic
1,3-ketoesters via oxidative O-cyclization reaction.
Pd(PPh3)2Cl2 was found to be the
crucial catalyst as its inclusion greatly enhanced the rate of the
reaction and cleanly afforded the products within minutes. Over 30
substrates were successfully converted to the desired compounds in
mostly moderate to good yields.