Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 18, Pages 8220-8230Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo3015424
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Funding
- National Science Foundation [CHE-0911264]
- Research Corporation for Science Advancement, Arnold
- Mabel Beckman Foundation Scholars Program, Donors of the American Chemical Society Petroleum Research Fund
- Calvin College
- Pomona College
- Major Research Instrumentation grant of the National Science Foundation [CHE-0922973]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [0922973, 0911264] Funding Source: National Science Foundation
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An efficient and inexpensive LiI-promoted O- to N-alkyl migration of 2-benzyloxy-, 2-allyloxy-, and 2-propargyloxypyridines and heterocycles is reported. The reaction produces the corresponding N-alkyl 2-pyridones and analogues under green, solvent-free conditions in good to excellent yields (30 examples, 20-97% yield). This method has been shown to be intermolecular and requires heat and lithium cation to occur.
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