Diastereodivergent Synthesis of Vinylsilanes Using Solid Silylzinc Reagent

Vinylsilanes are extensively utilized in organic synthesis, especially in stereospecific reactions. Silylmetalation has emerged as a highly effective alternative to hydrosilylation; however, the silylcopper and silylzinc reagents used are generally obtained from pyrophoric silyllithium or disilanes. We describe a catalyst-controlled diastereodivergent hydrosilylation employing novel solid reagents that eliminates the need for pyrophoric silyl lithium and is free of detrimental lithium ions. Catalytic copper produced the <i>E</i> isomer, whereas the <i>Z</i> isomer was formed with stoichiometric iron.