Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2016, Issue 25, Pages 4347-4353Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201600666
Keywords
Synthetic methods; Nucleophilic addition; Green chemistry; Vinylation; Nitrogen heterocycles; Calcium carbide; Acetylene gas
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Funding
- Thailand Research Fund [TRF-RSA5780055]
- National Nanotechnology Center (NANOTEC), NSTDA, Ministry of Science and Technology, Thailand through the Center of Excellence Network
- Grant for International Research Integration: Chula Research Scholar
- Postdoctoral Fellowship (Ratchadaphiseksomphot Endowment Fund)
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An efficient N-vinylation of indoles and O-vinylation of phenols to give N-vinyl indoles and phenyl vinyl ethers is reported. The vinylated products can be produced in satisfactory to excellent yields (65-92 %) upon treatment of indoles or phenols with calcium carbide in wet solvents in a standard laboratory setup. Key features of this reaction include the use of calcium carbide as a safe and inexpensive slow released acetylene source for N- and O-vinylation under simple reaction conditions without the need for metal catalyst or halogenated substrates.
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