Palladium-Catalyzed Cross-Coupling Reaction of 3-Iodoselenophenes with Boronic Acids

Abstract

The Suzuki cross-coupling of 3-iodoselenophenes with boronic acids in the presence of catalytic amount of palladium salt is described. This cross-coupling reaction proceeded cleanly under mild conditions and was performed with aryl boronic acids bearing electron-withdrawing, electron-donating, and neutral substituents, furnishing the correspondents products in moderate to good yields.

Key words

palladium - Suzuki cross-coupling - selenophene - boronic acid

References and Notes

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9

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 × 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, 3 H) ppm. ¹³C NMR (100 MHz, CDCl₃): δ = 148.25, 140.84, 136.57, 136.32, 136.17, 134.71, 129.58, 129.25, 129.21, 129.05, 129.01, 128.92, 128.38, 127.64, 127.19, 126.02, 21.19 ppm. MS: m/z (%) = 373 (100), 281 (65), 296 (45), 220 (42), 128 (72), 91 (65). HRMS: m/z calcd for C₂₃H₁₈Se: 374.0574; found: 374.0580.