Download PDF
Synlett 2001; 2001(12): 1881-1884
DOI: 10.1055/s-2001-18740
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.

P2-Et-Mediated Deprotonation of ortho-Halobenzyl Sulfones: Synthetic Applications as Zwitterionic Synthons

Ana Costa* , Carmen Nájera, José M. Sansano
  • *Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Alicante, Apdo. 99, 03080-Alicante, Spain; Fax: + 34(96)5903549; E-mail: cnajera@ua.es
Further Information

Publication History

Publication Date:
04 December 2001 (online)

  PDF Download  Permissions and Reprints All articles of this category

α-Sulfonyl benzylic carbanions, derived from ortho-halobenzyl sulfones 5 (Hal = Br, I), can be easily generated by the phosphazene base P2-Et and react with different electrophiles such as alkyl halides, aldehydes and ethyl acrylate. Palladium catalysed cross-coupling reactions performed at the halogen atom, followed by P2-Et-mediated alkylation-dehydrosulfinylation process using bromoacetates as electrophiles allow the preparation of ortho-substituted cinnamates.

sulfones - phosphazene bases - alkylations - aldol reaction - Heck reaction - cross-coupling

      >