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Synlett 2005(14): 2230-2232  
DOI: 10.1055/s-2005-872231
LETTER
© Georg Thieme Verlag Stuttgart · New York

Homocoupling Reactions Using Telluronium Salts

Kazunori Hirabayashi, Yuji Takeda, Toshio Shimizu, Nobumasa Kamigata*
Department of Chemistry, Graduate School of Science, Tokyo Metropolitan University, Minami-Ohsawa, Hachioji, Tokyo 192-0397, Japan
e-Mail: kamigata-nobumasa@c.metro-u.ac.jp;
Further Information

Publication History

Received 25 May 2005
Publication Date:
20 July 2005 (online)

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Abstract

The homocoupling reaction of aryldimethyltelluronium iodides in the presence of a catalytic amount of palladium(II) species and two equivalents of silver(I) acetate proceeded to afford the corresponding biaryls.

Key words

palladium - coupling - organometallic reagents - telluronium salt - silver(I) acetate

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5

General Procedure.
Palladium(II) chloride (0.05 mmol), silver(I) acetate (1.0 mmol), telluronium salt (0.5 mmol) and MeCN (3 mL) were placed in a dry screw-capped glass-tube. After stirring at 50 °C for 6-72 h, the resulting mixture was diluted with Et2O and passed through silica gel pad. The eluate was washed with 1 M HCl aq, NaHCO3 aq, and brine. The organic layer was dried over anhyd MgSO4, filtered, and concentrated under reduced pressure. The product was obtained in adequate purity. Further purification was performed with flash column chromatography on silica gel.

6

XRD Pattern of the Residue: 2θ (rel. intensity): 22.430 (746), 23.770 (696), 25.400 (342), 31.760 (159), 38.180 (1402), 39.280 (670), 42.730 (326), 44.380 (408), 46.400 (300), 59.380 (108), 64.500 (368), 77.460 (331).
Ag(0): 38.100 (98), 44.369 (60), 64.177 (43), 77.547 (100).
AgI: 22.337 (98), 23.675 (60), 25.321 (68), 32.775 (42), 39.204 (97), 42.624 (100), 45.584 (14), 46.312 (58), 59.303 (28).