Efficient nucleophilic substitution reactions of highly functionalized allyl halides in ionic liquid media

Tetrahedron Letters

Volumn 45, Issue 7, 2004, Pages 1427-1431

  Kotti, S R S Saibabu ^a   Xu, Xin ^a   Li, Guigen ^a   Headley, Allan D ^a  

^a TEXAS TECH UNIVERSITY   (United States)

Author keywords

Halides; Ionic liquid; SN2 reaction; , Unsaturated ketone

Indexed keywords

ALLYL COMPOUND; ANION; BORIC ACID; BUTYLMETHYLIMIDAZOLIUM TETRAFLUOROBORATE; FLUORINE DERIVATIVE; HALIDE; IMIDAZOLE DERIVATIVE; ION; KETONE DERIVATIVE; NITROGEN; ORGANIC SOLVENT; OXYGEN DERIVATIVE; SULFIDE; UNCLASSIFIED DRUG;

ARTICLE; INTERMETHOD COMPARISON; LIQUID; REACTION ANALYSIS; SYNTHESIS;

EID: 1642497631     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.12.051     Document Type: Article

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18. The synthesis of starting materials were conducted by following our published procedure as described in Ref. 1.
19. N2 nucleophlilic substitution reactions: Into a vial was loaded the substrate (0.51 mmol, 1.0 equiv) and ionic liquid (400 mg). The resulting mixture was stirred for 10 min and followed by the addition of the nucleophile (0.65 mmol, 1.3 equiv). The mixture was stirred at 45-50 °C for 2 h, and then cooled to room temperature. The product was extracted with diether ether (3 × 10 mL). The crude product is finally purified by silica column chromatography with EtOAc/hexane (4/1 v/v) as the eluent.