Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 12, Pages 5987-5998Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo400668v
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Funding
- National Science Foundation [CHE-0640729, CHE-0552292, CHE-1062944]
- Dreyfus Foundation
- Colby College
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1147787] Funding Source: National Science Foundation
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Acetylenes are increasingly versatile functional groups for a range of complexity-building organic transformations and for the construction of desirable molecular architectures. Herein we disclose a previously underappreciated aspect of arylacetylene reactivity by utilizing alkynes as electron-withdrawing groups (EWG) for promoting nucleophilic aromatic substitution (SNAr) reactions. Reaction rates for the substitution of 4-(fluoroethynyl)benzenes by p-cresol were determined by H-1 NMR spectroscopy, and these rate data were used to determine substituent (Hammett) constants for terminal and substituted ethynyl groups. The synthetic scope of acetylene-activated SNAr reactions is broad; fluoroarenes bearing one or two ethynyl groups undergo high-yielding substitution with a variety of oxygen and arylamine nucleophiles.
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