Hiyama coupling

The Hiyama coupling is a palladium-catalyzed cross-coupling reaction of organosilanes with organic halides used in organic chemistry to form carbon–carbon bonds (C-C bonds). This reaction was discovered in 1988 by Tamejiro Hiyama and Yasuo Hatanaka as a method to form carbon-carbon bonds synthetically with chemo- and regioselectivity. The Hiyama coupling has been applied to the synthesis of various natural products.

${\displaystyle {\begin{matrix}{}\\{\ce {{R-SiR''_{3}}+R'-X->[\mathrm {F^{-}} ][{\text{Pd cat.}}]R-R'}}\end{matrix}}}$

• ${\displaystyle {\ce {R}}}$: aryl, alkenyl or alkynyl
• ${\displaystyle {\ce {R'}}}$: aryl, alkenyl, alkynyl or alkyl
• ${\displaystyle {\ce {R''}}}$: Cl, F or alkyl
• ${\displaystyle {\ce {X}}}$: Cl, Br, I or OTf