Selectfluor-promoted fluorination of piperidinyl olefins

✍ Scribed by Meng-Yang Chang; Nien-Chia Lee; Ming-Fang Lee; Yu-Ping Huang; Chung-Han Lin

• Book ID: 104098261
• Publisher: Elsevier Science
• Year: 2010
• Tongue: French
• Weight: 798 KB
• Volume: 51
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2010.08.090

✦ Synopsis

A simple and straightforward synthesis of 1-substituted-4-aryl-5-fluoro-1,2,3,6-tetrahydropyridine (3) or 1-substituted 4-diarylmethanoyl-4-fluoropiperidine ( ) by the treatment of piperidinyl exo-or endo-olefin with 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate (Selectfluor) is reported. Two transformations from endo-olefin 1 to allylic fluoride 3 and from exo-olefin 2 to fluorohydrin 6 proceed via allylic fluorination and fluorohydroxylation in moderate yields. It presents two novel reactions promoted by Selectfluor and broadens the scope of application.