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Union of type II Anion Relay Chemistry (ARC) with Pd-induced Cross Coupling Reactions (CCR) has been achieved, in conjunction with the design, synthesis, and evaluation of a new class of bifunctional linchpins, comprising a series of vinyl silanes bearing beta- or gamma-electrophilic sites. The synthetic tactic permits both alkylation and Pd-mediated CCR of the anions derived via 1,4-silyl C(sp(2))--&gt;O Brook Rearrangements.

Uniting Anion Relay Chemistry with Pd-Mediated Cross Coupling: Design, Synthesis and Evaluation of Bifunctional Aryl and Vinyl Silane Linchpins