Table 1.

Oxidation Optimization

entry	oxidant	solvent	yieldb
1	o-chloranil (2 equiv)	THF	(<10)
2	TEMPO (1 mol %), NaOCl (aq.) (2 equiv)	CH2Cl2/H2O	0
3	TEMPO (1 mol %), Oxone (4 equiv)	CH2Cl2	(52)
4	TEMPO (1 mol %), n-Bu4NSO5c (2 equiv)	CH2Cl2	(59)
5	MnO2 (5 equiv)	MeOH	99
6	MnO2	CH2Cl2	98d
7	MnO2 19 mmol scale	CH2Cl2	98d

^a20 mol% A, 1.2 equiv DBU, 2-5 equiv methanol, 0.2 M in solvent.

^bIsolated yields (yields in parentheses calculated by GC with dodecane as an internal standard).

^cPrepared from commercial Oxone (see Supporting Information).

^d10 mol% A, 1.1 equiv DBU, 5 equiv methanol, 5 equiv MnO₂, 0.2 M in CH₂Cl₂.