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N-Vinylpyridinium tetrafluoroborate salts as reagents for the stereoselective and regioselective synthesis of symmetrical (2E,4E)-1,6-dioxo-2,4-dienes

✍ Scribed by Ge Gao; Neil Brown; Machiko Minatoya; Keith R. Buszek

Publisher: Elsevier Science
Year: 2008
Tongue: French
Weight: 188 KB
Volume: 49
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2008.08.076

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✦ Synopsis

We had previously demonstrated the utility of N-vinylpyridinium tetrafluoroborate salts as novel electrophilic coupling partners in Pd(0)-catalyzed Suzuki cross-coupling reactions with aryl and vinyl boronic acids. We now report that these crystalline, air-stable, and non-hygroscopic salts are also useful reagents for the synthesis of symmetrical (2E,4E)-1,6-dioxo-2,4-dienes (diene diones), which in turn are valuable starting materials for the synthesis of various five-membered heterocycles. The optimization of reaction conditions and the scope and limitations of the reductive dimerization are discussed.

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