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

Won Suk Kim; Hyung Jin Kim; Cheon Gyu Cho

doi:10.1021/ja037043a

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

Won Suk Kim, Hyung Jin Kim, Cheon Gyu Cho

Department of Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

82 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 language	English
Pages (from-to)	14288-14289
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	125
Issue number	47
DOIs	https://doi.org/10.1021/ja037043a
State	Published - 26 Nov 2003

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

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.",

author = "Kim, {Won Suk} and Kim, {Hyung Jin} and Cho, {Cheon Gyu}",

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AU - Cho, Cheon Gyu

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Y1 - 2003/11/26

N2 - 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.

AB - 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.

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ER -

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

Abstract

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