LETTER
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Cross-Coupling Reaction of 3-Iodoselenophenes with Boronic Acids
125
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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)
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Yield 0.088 g (95%). 1H NMR (400 MHz, CDCl3): d = 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): d = 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.
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Synlett 2008, No. 1, 119–125 © Thieme Stuttgart · New York