Download PDF
Synlett 2001; 2001(3): 0374-0378
DOI: 10.1055/s-2001-11389
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Heteroaryl-N-difluoromethyltrimethylsilanes - Versatile Sources of Heteroaryl-N-difluoromethyl Anions in Reactions with Carbonyl Compounds

German Bissky* , Vasilij I. Staninets, Alexander A. Kolomeitsev, Gerd-Volker Röschenthaler
  • *Institut für Anorganische & Physikalische Chemie, Universität Bremen, Leobener Strasse, 28334 Bremen, Germany; Fax + 49(4 21)218-42 67; E-mail: alex@chemie.uni-bremen.de; gvr@chemie.uni-bremen.de
Further Information

Publication History

Publication Date:
31 December 2001 (online)

  PDF Download  Permissions and Reprints All articles of this category

An efficient procedure for synthesizing heteroaryl-N-difluoromethyltrimethylsilanes - new nucleophilic difluoromethylene synthons - from easily available N-bromodifluoromethylated heterocycles, chlorotrimethylsilane and aluminium powder in triglyme or N-methylpyrrolidinone on a preparative scale in 71-75% isolated yield is described. Heteroaryl-N-difluoromethyltrimethylsilanes and benzaldehyde react under fluoride ion catalysis to give 1-(1,1-difluor-2-hydroxy-2-phenyl-ethyl)heteroaryls, whereas for anionic heteroaryl-N-difluoromethylation of cyclohexanone a stoichiometrical mixture of heteroaryl-N-difluoromethyltrimethylsilanes and tetramethylammonium fluoride has to be used.

heteroaryl-N-difluoromethyltrimethylsilanes - carbanion trapping - anionic heteroaryl-N-difluoromethylation - tetramethylammonium fluoride