Unification of Anion Relay Chemistry with the Takeda and Hiyama Cross-Coupling Reactions: Identification of an Effective Silicon-Based Transfer Agent

Abstract

The unification of Anion Relay Chemistry
(ARC) with the Takeda and Hiyama palladium-mediated
cross-coupling processes to provide aryl−aryl, alkenyl−
aryl, and alkenyl−alkenyl coupled products by exploiting a
common silicon-based transfer agent has been achieved.
These results provide a practical solution for intermolecular
cross-coupling of organolithium reagents without
the problematic lithium−halogen exchange and/or undesired
homocoupling that has kept organolithium crosscouplings
from achieving the same level of utility as
other palladium-mediated methods (e.g., Suzuki organoboron,
Negishi organozinc, Stille organotin, Kumada organomagnesium,
etc.).