Mechanism
The organosilane is activated with fluoride (as some sort of salt such as TBAF or TASF) or a base to form a pentavalent silicon center which is labile enough to allow for the breaking of a C-Si bond during the transmetalation step. The general scheme to form this key intermediate is shown below. This step occurs in-situ, or at the same time as the catalytic cycle in the reaction.
The mechanism for the Hiyama-coupling follows a catalytic cycle, including an A) oxidative addition step, in which the organichalide adds to the palladium oxidizing the metal from palladium(0) to palladium(II); a B) transmetalation step, in which the C-Si bond is broken and the second carbon fragment is bound to the palladium center; and finally C) a reductive elimination step, in which the C-C bond is formed and the palladium returns to its zero-valent state to start the cycle over again. The catalytic cycle is shown below.
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