Benzo(B)Thiophene → bis[4-(1-benzothien-2-yl)-2-methyl-1H-inden-1-yl](dimethyl)silane

Participants

Reaction Steps

In an argon atmosphere, to a solution of 1.74 g (13.0 mmol) of benzothiophene in 30 ml of THF, 5.24 ml of 2.5 M nBuLi (13.0 mmol) in hexanes was added at ambient temperature. This mixture was stirred for 2 hours, and, then, 29.0 ml of 0.5 M ZnCl2 (14.5 mmol) in THF was added. The resulting mixture was stirred for 1 hour. Then, 10.0 ml of 0.02 M Pd(PtBu3)2 (0.20 mmol, 4 mol. %) in THF and 2.37 g (5.0 mmol) of 1 were added. This mixture was stirred for 5 hours at reflux. The product was isolated by flash chromatography on Silica Gel 60 (40-63 μm, d 30 mm, l 100 mm; eluent: hexanes). Yield 2.76 g (95%) of white solid of ca. 1 to 1 mixture of rac- and meso-compounds.

Provenance & Evidence