title: Transition-metal-free carbofluorination of TBS-protected nitrogen-containing cyclic enynols: synthesis of fluorinated azabicycles.
abstract: The synthesis of fluorinated azabicycles from tert-butyldimethylsilyl-protected N-containing cyclic enynols using inexpensive BF3·OEt2 is described. In this reaction, BF3 reacts as both the Lewis acid and the fluoride source for cyclization/fluorination of the TBS-protected cyclic N-containing enynols. The method provides an easy access to fluorinated azabicycles where a new C(sp(2))-F bond and a new bicyclic skeleton are generated at ambient temperature within 1-13 min under metal-free reaction conditions.
authors.affiliation: Department of Chemistry, National Taiwan Normal University, 88 Ding-Jou Road, Section 4, Taipei 11677, Taiwan, Republic of China. cheyeh@ntnu.edu.tw
authors.forename: Ming-Chang P
authors.initials: MC
authors.lastname: Yeh
authors.forename: Chia-Jung
authors.initials: CJ
authors.lastname: Liang
authors.forename: Tzu-Lin
authors.initials: TL
authors.lastname: Huang
authors.forename: Hsiao-Ju
authors.initials: HJ
authors.lastname: Hsu
authors.forename: Yu-Shuo
authors.initials: YS
authors.lastname: Tsau
mesh_terms: D053961:Azabicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D003511:Cyclohexanols / Q000737:chemistry*; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*
chemical_list: D053961:Azabicyclo Compounds; D003511:Cyclohexanols; D012821:Silanes; C103256:tert-butyldimethylsilane; D009584:Nitrogen