Homocoupling Reactions Using Telluronium Salts

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.

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

References

1a Metal-Catalysed Cross-Coupling Reactions   Diederich F. Stang P. Wiley-VCH; Weinheim: 1998. 

1b Tsuji J. Palladium Reagents and Catalysts. Innovations in Organic Synthesis   Wiley-VCH; New York: 1995. 

1c Tsuji J. Transition Metal Reagents and Catalysts. Innovations in Organic Synthesis   Wiley-VCH; New York: 2000. 

For recent reports about palladium-catalyzed homocoupling reaction using organometallic reagents, see:

2a Yoshida H. Yamaryo Y. Ohshita J. Kunai A. Tetrahedron Lett.  2003,  44:  1541 

2b Yoshida H. Yamaryo Y. Ohshita J. Kunai A. Chem. Commun.  2003,  1510 

2c Li JH. Xie YX. Yin DL. J. Org. Chem.  2003,  68:  9867 ; and references cited therein

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See also:

3g Bergman J. Tetrahedron  1972,  28:  3323 

3h Bergman J. Carlsson R. Sjöberg B. Org. Synth. Coll. Vol. VI  1988,  468 

4 Hirabayashi K. Nara Y. Shimizu T. Kamigata N. Chem. Lett.  2004,  33:  1280 

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).

7a Ozawa F. Fujimori M. Yamamoto T. Yamamoto A. Organometallics  1986,  5:  2144 

7b Ozawa F. Hidaka T. Yamamoto T. Yamamoto A. J. Organomet. Chem.  1987,  330:  253 

7c See also: Scott JD. Puddephatt RJ. Organometallics  1983,  2:  1643