Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 45, Pages 15951-15954Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201502912
Keywords
cyclization; indoles; radicals; reductions; samarium diiodide; solvent effects
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Funding
- Alexander von Humboldt Foundation
- Deutsche Forschungsgemeinschaft
- Bayer HealthCare
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New conditions for dearomatizing samarium-ketyl (hetero)arene cyclizations are reported. In many examples of these samarium diiodide-mediated reactions, lithium bromide and water can be used as additives instead of the carcinogenic and mutagenic hexamethylphosphoramide (HMPA). The best results were obtained for the cyclizations of N-acylated indole derivatives delivering the expected indolines in good yields and excellent diastereoselectivities. A new type of cyclization delivering indolyl-substituted allene derivatives is also described. The scope and limitations of the lithium bromide/water system are discussed.
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