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DOI: 10.1055/s-2003-41499
A Convenient Preparation of Chalcogenoenynes from β-Bromovinyl Ketene Chalcogenoacetals
Publication History
Publication Date:
19 September 2003 (online)
Abstract
β-Bromovinyl ketene chalcogenoacetals have been synthesized stereoselectively via electrophilic addition of the benzeneselenenyl bromide to substituted alkynes. The palladium-catalyzed cross-coupling reaction of β-bromovinyl ketene chalcogenoacetals with 1-alkynes gave the corresponding chalcogenoenynes in 62-85% yields
Key-words
cross-coupling - chalcogenoenynes - palladium - tellurium - selenium - β-bromovinyl ketene chalcogenoacetals
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References
Pd(0) Catalyzed Cross-Coupling Reaction of β-Bromovinyl Ketene Chalcogenoacetals 2b with 1-Hexyne; General Procedure: To a solution of Pd(PPh3)
(5 mol%, 0.058 g), in pyrrolidine (5 mL) at r.t. under Ar atmosphere, were added of β-bromovinyl ketene chalcogenoacetals 2b (0.425 g, 1 mmol) and hexyne (0.164 g, 2 mmol). The mixture was stirred at r.t. for 10 h, treated with NH4Cl saturated solution (5 mL) and then extracted with EtOAc. The organic layer was washed with brine and dried over MgSO4. The solvent was evaporated and the residue was purified by flash silica gel chromatography eluted with hexane to yield 3a in 65% yield (0.276 g). 1H NMR (200 MHz, CDCl3): δ = 7.74-7.41 (m, 2 H), 7.39-7.25 (m, 3 H), 2.46 (s, 3 H), 2.40 (t, J = 7.0 Hz, 2 H,), 1.63-1.25 (m, 8 H), 1.35-1.06 (m, 4 H), 0.95 (t, J = 7.0 Hz, 3 H), 0.92 (t, J = 7.0 Hz, 3 H). 13C NMR (50 MHz, CDCl3): δ = 140.56, 135.02, 129.32, 128.85, 127.77, 116.11, 98.89, 76.90, 33.87, 31.13, 30.69, 28.11, 22.14, 21.95, 19.28, 16.70, 13.81, 13.50. IR (neat, cm-1): 2929, 2859, 2360, 1699, 1377. LRMS (rel. int.): m/z = 426 (10), 332 (48) 270 (100), 176 (30), 71 (42), 57 (38).