Table 1.

Scope of the coupling of alkyl- and arylboronic acids to 1,4-benzoquinone.^a

^aBenzoquinone (0.25 mmol), boronic acid (0.375 mmol), AgNO₃ (0.05 mmol), K₂S₂O₈ (0.75 mmol), 23 °C, 3–12 h; isolated yields of chromatographically and spectroscopically pure products yields displayed, unless otherwise noted. (NH₄)₂S₂O₈ is also suitable as an oxidant.

^bYield of the reaction performed on gram-scale with no organic solvent (see Figure 2).

^cProducts were unstable to several isolation conditions, but proved relatively stable in solution after extraction. See Supporting Information for more details.