Table 1. Oxidative Condensation of 4-Chloro-1,2,3-benzenetriol (9) with N-Methylbenzene-1,2-diamine (4)^a.

entry	oxidant	additive	yield (%)b
1c	O2		12
2d	1,4-benzoquinone		10
3d	o-chloranil		trace
4e	O2	Na2CO3	5
5e	O2	K2CO3	10
6e	O2	Cs2CO3	17

^aUnless otherwise noted, reactions were performed using 4 (0.246 mmol) and 9 (1.0 equiv) in 2-propanol (2.0 mL).

^bIsolated yield.

^cThe reaction was performed at room temperature (rt) under an oxygen atmosphere.

^dThe reaction was performed at 0 °C under an argon atmosphere using the oxidant (3.0 equiv) indicated.

^eThe reaction was performed at rt under an oxygen atmosphere using the additive (1.0 equiv) indicated.