Regioselectivity in the Stille Coupling Reactions of 3,5-Dibromo-2-pyrone

Won Suk Kim, Hyung Jin Kim, Cheon Gyu Cho

Research output: Contribution to journalArticlepeer-review

75 Scopus citations

Abstract

The Stille couplings of 3,5-dibromo-2-pyrone normally take place regioselectively at C3, lower in electron density than C5, thus oxidative addition proceeds faster . When the reactions are carried out with Cu(I) in DMF or other polar aprotic solvent, however, the couplings occur predominantly at C5. The observed regiochemical reversal is attributed to the preferred formation of 5-pallado-2-pyrone intermediate which, in addition, turned out to be more reactive than 3-pallado-2-pyrone intermediate.

Original languageEnglish
Pages (from-to)14288-14289
Number of pages2
JournalJournal of the American Chemical Society
Volume125
Issue number47
DOIs
StatePublished - 26 Nov 2003

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