Palladium-catalyzed cross-alkynylation of aryl bromides by sodium tetraalkynylaluminates

Dmitri Gelman, Dmitry Tsvelikhovsky, Gary A. Molander, Jochanan Blum*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

44 Scopus citations


Sodium tetraalkynylaluminates (1-4), prepared from NaAlH4 and terminal alkynes, cross-couple with aryl bromides in the presence of Pd(0) and Pd(II) catalysts. The reactions take place in boiling THF or DME. The process is applicable to both homo- and heterocyclic aryl bromides and can be used for conversion of polybromo compounds into polyalkynes. The reactions are high yielding and selective, free of undesired homocoupling and hydrogenolysis processes. The reagents selectively react with the ring-bound bromine atoms but do not affect chloro, cyano, triflate, or ester functions.

Original languageAmerican English
Pages (from-to)6287-6290
Number of pages4
JournalJournal of Organic Chemistry
Issue number18
StatePublished - 6 Sep 2002


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