Palladium-catalyzed cross-coupling of five-membered heterocyclic silanolates

Scott E. Denmark, John D. Baird, Christopher S. Regens

Research output: Contribution to journalArticlepeer-review


(Chemical Equation Presented) The preparation of π-rich 2-aryl heterocycles by palladium-catalyzed cross-coupling of sodium heteroarylsilanolates with aryl iodides, bromides, and chlorides is described. The cross-coupling process was developed through extensive optimization of the following key variables: (1) identification of stable, isolable alkali metal silanolates, (2) identification of conditions for preformation and isolation of silanolate salts, (3) judicious choice in the palladium catalyst/ligand combination, and (4) selection of the protecting group on the nitrogen of indole. It was found that the alkali metal silanolates, either isolated or formed in situ, offered a significant rate enhancement and broader substrate scope over the use of silanols activated by Brønsted bases such as NaOt-Bu. In addition, the optimized conditions for the cross-coupling of 2-indolylsilanolates were readily applied to the cross-coupling of 2-pyrrolyl-, 2-furyl-, and 2-thienylsilanolates.

Original languageEnglish (US)
Pages (from-to)1440-1455
Number of pages16
JournalJournal of Organic Chemistry
Issue number4
StatePublished - Feb 15 2008

ASJC Scopus subject areas

  • Organic Chemistry


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