Table 1.

Catalytic oxidative carbon-carbon bond cleavage of glycerol with various oxidizing agents in the presence of Pd catalysts at room temperature.^a

entry	catalyst	oxidant	yield (%)d	2/3 (× 10−5 mol)e
1	PdCl2	H2O2	trace	trace/trace
2	Pd(OAc)2	H2O2	6	0.16/0.20
3	4	H2O2	41	1.50/8.05
4	4	t-BuO2H	trace	-/-
5b	4	Oxone	10	0.39/1.52
6	4	K2S2O8	-	-/-
7c	4	O2	-	-/-

^aAll reactions were performed with glycerol (10 mg, 10.8 × 10⁻⁵ mol), Pd catalyst (5 mol%). Entry 1–3: 30% H₂O₂ (0.4 mL) in H₂O (0.1 mL) was added. In the entry 4, tBuOOH (70% in H₂O, 0.4 mL) was used. Entries 5~6: 10.8 × 10⁻⁵ mol of oxidant (entry 5: oxone, entry 6: K₂S₂O₈) in 0.3 mL of H₂O was used. Entry 7: O₂ was bubbled in 0.3 mL of H₂O solution. All reactions were performed at room temperature for 6 hours..

^bRun in H₂O (0.4 mL).

^cContinuous flow with O₂.

^dConversion yield of glycerol.

^eThe amount of each product was determined by ¹H NMR spectral analysis using MeOH as the internal standard.⁸