Synthesis of unsaturated organotrifluoroborates via Wittig and Horner-Wadsworth-Emmons olefination.
The stereoselective synthesis of unsaturated organotrifluoroborates by using the Wittig and Horner-Wadsworth-Emmons olefination is described. These reactions were general for both alkyl- and aryltrifluoroborates. The synthesis of di- and trisubstituted olefins was achieved by using formyl- and acetyl-substituted organotrifluoroborates. The products were isolated in moderate to excellent yield. The Wittig reaction with nonstabilized ylides was performed under salt free conditions in most cases to obtain the Z-isomer. The E-isomer was accessed by using preformed stabilized ylides. The Horner-Wadsworth-Emmons reaction also gave the E-isomer as expected.
Molander
Gary A
GA
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA. gmolandr@sas.upenn.edu
Figueroa
Ruth
R
D000475:Alkenes / Q000737:chemistry*; D001881:Borates / Q000737:chemistry*; D005461:Fluorine / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D063065:Organophosphonates / Q000737:chemistry; D011188:Potassium / Q000737:chemistry
D000475:Alkenes; D001881:Borates; D063065:Organophosphonates; D005461:Fluorine; D011188:Potassium