C-F bond cleavage by intramolecular S(N)2 reaction of alkyl fluorides with O- and N-nucleophiles

Laijun Zhang; Wei Zhang; Jun Liu; Jinbo Hu

doi:10.1021/jo802819p

C-F bond cleavage by intramolecular S(N)2 reaction of alkyl fluorides with O- and N-nucleophiles

J Org Chem. 2009 Apr 3;74(7):2850-3. doi: 10.1021/jo802819p.

Authors

Laijun Zhang¹, Wei Zhang, Jun Liu, Jinbo Hu

Affiliation

¹ Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai 200032, China.

PMID: 19323576
DOI: 10.1021/jo802819p

Abstract

The nucleophilic substitution of alkyl fluorides was achieved in the intramolecular reactions with O- and N-nucleophiles. The intramolecular defluorinative cyclization reaction was influenced by the nature of nucleophiles, the size of the ring to be formed, and the comformational rigidity of the precursors. Intermolecular nucleophilic substitution reactions of alkyl fluorides under similar reaction conditions were found to be difficult. The stereochemistry study of the current C-F bond cleavage reaction showed a complete configurational inversion, which supports an intramolecular S(N)2 reaction mechanism.