Regioselective Stille coupling reactions of 3,5-dibromo-2-pyrone with various aryl and vinyl stannanes

Won Suk Kim, Hyung Jin Kim, Cheon-Gyu Cho

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

3,5-Dibromo-2-pyrone underwent facile regioselective Stille coupling reactions with aryl, heteroaryl and vinyl stannanes to produce various 3-substituted, 5-bromo-2-pyrones. Addition of a catalytic amount of CuI greatly increased the selectivity and chemical yield of the desired 3-aryl-5-bromo-2-pyrone. Second Stille coupling reactions on the resulting 3-aryl-2-pyrones gave rise to a series of potentially useful 2-pyrones with two different functionalities at C3 and C5 position in good to excellent isolated yields. 2-Pyrones with pyridyl groups at C3 position can undergo Lewis acid catalyzed Diels-Alder cycloaddition reactions with benzyl vinyl ether.

Original languageEnglish
Pages (from-to)9015-9017
Number of pages3
JournalTetrahedron Letters
Volume43
Issue number50
DOIs
StatePublished - 2002 Dec 9

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Cycloaddition Reaction
Lewis Acids
Cycloaddition
stannane
3,5-dibromo-2-pyrone
2-pyrone
vinyl ether

Cite this

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title = "Regioselective Stille coupling reactions of 3,5-dibromo-2-pyrone with various aryl and vinyl stannanes",
abstract = "3,5-Dibromo-2-pyrone underwent facile regioselective Stille coupling reactions with aryl, heteroaryl and vinyl stannanes to produce various 3-substituted, 5-bromo-2-pyrones. Addition of a catalytic amount of CuI greatly increased the selectivity and chemical yield of the desired 3-aryl-5-bromo-2-pyrone. Second Stille coupling reactions on the resulting 3-aryl-2-pyrones gave rise to a series of potentially useful 2-pyrones with two different functionalities at C3 and C5 position in good to excellent isolated yields. 2-Pyrones with pyridyl groups at C3 position can undergo Lewis acid catalyzed Diels-Alder cycloaddition reactions with benzyl vinyl ether.",
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Regioselective Stille coupling reactions of 3,5-dibromo-2-pyrone with various aryl and vinyl stannanes. / Kim, Won Suk; Kim, Hyung Jin; Cho, Cheon-Gyu.

In: Tetrahedron Letters, Vol. 43, No. 50, 09.12.2002, p. 9015-9017.

Research output: Contribution to journalArticle

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AB - 3,5-Dibromo-2-pyrone underwent facile regioselective Stille coupling reactions with aryl, heteroaryl and vinyl stannanes to produce various 3-substituted, 5-bromo-2-pyrones. Addition of a catalytic amount of CuI greatly increased the selectivity and chemical yield of the desired 3-aryl-5-bromo-2-pyrone. Second Stille coupling reactions on the resulting 3-aryl-2-pyrones gave rise to a series of potentially useful 2-pyrones with two different functionalities at C3 and C5 position in good to excellent isolated yields. 2-Pyrones with pyridyl groups at C3 position can undergo Lewis acid catalyzed Diels-Alder cycloaddition reactions with benzyl vinyl ether.

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