An efficient and simple method for the oxidative coupling of benzylic and allylic sp3 C–H bonds with active methylenic sp3 C–H bonds under metal-free conditions was developed by employing 2, 3-dichloro-5, 6-dicyanobenzoquinone (DDQ) as an oxidant. The reaction was shown to proceed smoothly for various 1, 3-dicarbonyl compounds with a range of benzylic and allylic substrates in good to excellent yields.