Sodium Carbonate → Biphenyl

Participants

Reaction Conditions

Reaction Steps

Complexes 7a, 7b, 7c are used for Suzuki coupling reaction of iodobenzene and benzeneboronic acid, as shown in scheme 2, above. Iodobenzene (2.5 mmol, 1 equiv.), benzeneboronic acid (2.75 mmol, 1.1 equiv.), Na2CO3 (560 mg, 5.28 mmol, 2.1 equiv.), palladium complex (0.03 mmol) and water (2.5 ml) are mixed with [C4mim][BF4] (5 ml). The mixture is heated to 110° C. with vigorous stirring for 12 hours, then cooled and extracted with diethyl ether (3×15 ml). The combined organic phase is dried over MgSO4 and filtered. The product, biphenyl, is obtained in 100% yield. If a nitrile ionic liquid, [C3CNmim][BF4], is used in place of the [C4mim][BF4], a similar yield is obtained. Significantly, using [C3CNmim][BF4] the yields can be maintained at above 90% even after six runs of catalysis, while yields decrease rapidly for [C4mim][BF4]. Dissolving PdCl2 in the [C3CNmim][BF4] gives the same result as using complexes 6 and 7.

Provenance & Evidence