Unification of anion relay chemistry with the Takeda and Hiyama cross-coupling reactions: Identification of an effective silicon-based transfer agent

Amos B. Smith, Adam T. Hoye, Dionicio Martinez-Solorio, Won Suk Kim, Rongbiao Tong

Research output: Contribution to journalArticlepeer-review

53 Scopus citations

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 cross-couplings from achieving the same level of utility asother palladium-mediated methods (e.g., Suzuki organoboron, Negishi organozinc, Stille organotin, Kumada organomagnesium, etc.).

Original languageEnglish
Pages (from-to)4533-4536
Number of pages4
JournalJournal of the American Chemical Society
Volume134
Issue number10
DOIs
StatePublished - 14 Mar 2012

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