Synthesis of glycosyl fluorides from thio-, seleno-, and telluroglycosides and glycosyl sulfoxides using aminodifluorosulfinium tetrafluoroborates.
Glycosyl fluorides can be synthesized from thio-, seleno-, and telluroglycosides and glycosyl sulfoxides using the aminodifluorosulfinium tetrafluoroborate reagents Xtalfluor-E and -M, with or without added N-bromosuccinimide. Mechanistic studies provide evidence that fluoride is delivered from the tetrafluoroborate counterion.
School of Chemistry and Bio21 Institute of Molecular Science and Biotechnology, University of Melbourne, 30 Flemington Rd., Parkville 3010, Australia.
Sammi
S
Tsegay
Rohan J
RJ
Williams
Spencer J
SJ
Williams
D005025:Ethylene Dichlorides / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis*; D054879:Halogenation; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry; D016566:Organoselenium Compounds / Q000737:chemistry; D012997:Solvents / Q000737:chemistry; D013454:Sulfoxides / Q000737:chemistry; D013457:Sulfur Compounds / Q000737:chemistry; D013691:Tellurium / Q000737:chemistry; D013865:Thioglycosides / Q000737:chemistry
D005025:Ethylene Dichlorides; D006027:Glycosides; D006845:Hydrocarbons, Fluorinated; D009942:Organometallic Compounds; D016566:Organoselenium Compounds; D012997:Solvents; D013454:Sulfoxides; D013457:Sulfur Compounds; D013865:Thioglycosides; C551695:diethylaminodifluorosulfinium tetrafluoroborate; C551696:morpholinodifluorosulfinium tetrafluoroborate; D013691:Tellurium