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General Procedure for the Cross-Coupling Reaction To a solution of appropriate 3-iodoselenophene (0.25 mmol) in DME (2.5 mL) was added Pd(OAc)2 (0.003g, 5 mol, and boronic acid (0.35 mmol) under argon. The resulting solution was stirred for 30 min at r.t. After this time, a solution of K3PO4 (1.2 mmol, 0.254 g) in H2O (0.6 mL) was added. The mixture was then heated at reflux during 1-15 h, cooled to r.t, diluted with CH2Cl2 (20 mL, and washed with brine (2 x 20 mL, The organic phase was separated, dried over MgSO4, and concentrated under vacuum. The residue was purified by flash chromatography on silica gel using hexane as eluent. Selected Spectral and Analytical Data for 2,5-(Diphenyl)-3-(p-tolyl)selenophene (3a) Yield 0.088 g (95, 1H NMR (400 MHz, CDCl3, δ, 7.59-7.57 (m, 3 H, 7.39-7.35 (m, 2 H, 7.30-7.19 (m, 8 H, 7.10-7.08 (m, 2 H, 2.33 s
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18Se: 374.0574; found: 374.0580.
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