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 journalArticlepeer-review

29 Scopus citations

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 - 9 Dec 2002

Fingerprint

Dive into the research topics of 'Regioselective Stille coupling reactions of 3,5-dibromo-2-pyrone with various aryl and vinyl stannanes'. Together they form a unique fingerprint.

Cite this