Cross-coupling reactions alkylsilane

Alkylsilanes activated in situ by TBAF are also applicable to the cross-coupling reaction with aryl halides (Scheme The fact that the reaction requires excess... 

The cross-coupling reaction of an optically active alkylsilane gives us valuable information on the stereochemistry in transmetallation. The reaction of (5)-l-phenyl-1-(trifluorosilyl)ethane (34% ee) with 4-acetylphenyl triflate in the presence of 5 mol % of Pd(PPh3>4 and TBAF (2 equiv) at 50 °C gave (5)-1-phenyl-l-(4-acetylphenyl)ethane of 33% ee with nearly complete retention of configuration. At higher temperatures, ee of the product decreased linearly, and above 75 °C inversion of configuration predominated (Scheme 26). Similar temperature dependency was observed also in the reaction of 3-formylphenyl triflate. 

Of-Silylalkanenitriles couples with aryl halides to give a variety of cx-arylalkanenitriles (Scheme 3-169). On the other hand, alkyl cross-coupling reaction using alkylsilane reagents as nucleophiles is successful only with... 

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