Journal
GREEN CHEMISTRY
Volume 12, Issue 10, Pages 1772-1782Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c0gc00274g
Keywords
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Funding
- National Natural Science Foundation of China [20903042]
- Analytical and Testing Center of HUST
- Program for new Century Excellent Talents in the University of China [NCET-10-0383]
- Hubei provincial government
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Water proved to be an efficient solvent for oxidation of a Baylis-Hillman adduct with IBX. The generated product, a methylene intermediate, could be trapped in situ by many nucleophiles in water, such as styrenes, beta-dicarbonyl compounds, benzamide and less reactive indoles. This strategy offers an alternative way to methylenylation of beta-dicarbonyl compounds with formaldehyde for the formation of a methylene intermediate, thus allows the use of some nucleophiles that are chemically unstable to formaldehyde. The use of water as solvent, good recycling ability of IBX oxidant and wide substrate scopes make these reactions very attractive from the viewpoint of green chemistry.
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