Butyldimethylsilyl diphenylphosphine

This coupling reaction could also be carried out by using a catalytic amount of CsF in DMF (eq 4). The silyl ether of the adduct is initially formed by catalytic transfer of the silyl group from the silylphosphine to an intermediate cesium alkoxide, which following hydrolysis gave the same coupling product as above (eq 4).  

Lewis-acid-catalyzed/mediated Phosphination. The silylphosphine smoothly reacted with electrophiles activated by a Lewis acid. Addition of the silylphosphine to the activated pro-piolates also proceeded to produce vicinal s yn-silylphosphinated acrylates (eq 5).  

In the presence of Lewis acids such as EtsAl, EtaAlCl, and BF3 OEt2, the silylphosphine reacted with aldehydes and epoxides to give the corresponding a- and /3-hydroxyalkylphosphine derivatives, respectively (eqs 6 and 7)5 The more substituted alkylphosphine was preferentially formed by using an unsymmetrical epoxide. This is in contrast to the basic phosphination of epoxides, which provides mainly less substituted alkylphosphines.  

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To a solution of (tert-butyldimethylsilyl)diphenylphosphine (72mg, 0.24mmol) and styrene (21 mg, 23 pL, 0.20mmol) in DMF (1.5ml) was added dropwise a 1M TBAF solution in THF (240 pL, 0.24 mmol) at room temperature. After stirring for 15 min at room temperature, the solvent was removed under vacuum. The residue was purified by a column chromatography on silica gel (CHCl3/Hex= 1 4, R =0.4) to give the addition product (47 mg, 89%) as a colorless oil. 

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