FUNCTIONALIZATION OF A NON ACTIVATED C-H BOND - FLUORINATION OF VINDOLINE AT C-20 IN SUPERACIDS

Authors
BERRIER C JACQUESY JC JOUANNETAUD MP LAFITTE C VIDAL Y ZUNINO F FAHY J DUFLOS A
Citation
C. Berrier et al., FUNCTIONALIZATION OF A NON ACTIVATED C-H BOND - FLUORINATION OF VINDOLINE AT C-20 IN SUPERACIDS, Tetrahedron, 54(45), 1998, pp. 13761-13770
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
45
Year of publication
1998
Pages
13761 - 13770
Database
ISI
SICI code
0040-4020(1998)54:45<13761:FOANAC>2.0.ZU;2-E
Abstract
Reaction of vindoline 1a with NBS, NCS, H2O2 in HF-SbF5 yields 7 beta substituted (Br, Cl or OH)-20-fluoro-6,7-dihydrovindolines. These resu lts imply reaction of the electrophile (Br+, Cl+ and OH+ equivalent) o n the beta-face of C-6-C-7 double bond to give oniums ions, followed b y a 1,3-hydride shift from C-20 to Cd, and fluorination of the resulti ng ion. (C) 1998 Elsevier Science Ltd. All rights reserved.