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. 2016 Oct 13;18(20):5432–5435. doi: 10.1021/acs.orglett.6b02862

Table 1. C–H Arylation Catalyst Optimizationa.

graphic file with name ol-2016-02862y_0009.jpg

entry catalyst 3ab (%)
1 [Ru(p-cymene)Cl2]2 (4 mol %) nd
2 NiBr2·diglme/dtbbpy (4 mol %) nd
3 [Ru(p-cymene)Cl2]2 (4 mol %) and NiBr2·diglme/dtbbpy (4 mol %) 45
4 [Ru(p-cymene)Cl2]2 (4 mol %) and dtbbpy (4 mol %) 48
5 [Ru(p-cymene)Cl2]2 (4 mol %) and PCy3 (8 mol %) 91 (94c)
6 RuCl3·3H2O (8 mol %) and PCy3 (8 mol %) 68
a

Reactions run with 2-methylbenzoic acid 1a (0.25 mmol) and 2a (1.5 equiv).

b

GC yield of methyl ester, uncorrected.

c

Isolated yield of methyl ester. Dtbbpy = 4,4′-di-tert-butyl-2,2′-bipyridine.