The Use of Fluoride as a Leaving Group: SN2′ Displacement of a CF Bond on 3,3-Difluoropropenes with Organolithium Reagents To Give Direct Access to Monofluoroalkenes

✍ Scribed by Maxime Bergeron; Thomas Johnson; Prof. Jean-François Paquin

• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: English
• Weight: 354 KB
• Volume: 50
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.201105138

✦ Synopsis

Typical procedure: A solution of nBuLi (2.6 m in hexanes, 0.33 mmol) was slowly added to a solution of 1 (50 mg, 0.28 mmol) in THF (2.5 mL) at À78 8C. The mixture was stirred for 2 h before being quenched with drops of water. The mixture was poured into saturated aqueous NaHCO 3 and extracted with Et 2 O (3 ). The combined organic layers were washed with brine, dried over MgSO 4 , and concentrated. The resulting colorless liquid 2 (59 mg, 97 %) was characterized without further purification.