Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 5, Pages 2231-2233Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo802713y
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Funding
- National Institutes of Health [GM39764]
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Ortholithiations of a range of arenes mediated by lithium dilsopropylamide (LDA) in THF at -78 degrees C reveal substantial accelerations by as little as 0.5 mol % of LiCl (relative to LDA). Substrate dependencies suggest a specific range of reactivity within which the LiCl catalysis is optimal. Standard protocols with unpurified commercial samples of n-butyllithium to prepare LDA or commercially available LDA show marked batch-dependent rates-up to 100-fold-that could prove significant to the unwary practitioner. Other lithium salts elicit more modest accelerations. The mechanism is not discussed.
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