P-2-Et-mediated deprotonation of ortho-halobenzyl sulfones: Synthetic applications as zwitterionic synthons

Authors
Costa, A Najera, C Sansano, JM
Citation
A. Costa et al., P-2-Et-mediated deprotonation of ortho-halobenzyl sulfones: Synthetic applications as zwitterionic synthons, SYNLETT, (12), 2001, pp. 1881-1884
Citations number
31
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
12
Year of publication
2001
Pages
1881 - 1884
Database
ISI
SICI code
0936-5214(200112):12<1881:PDOOSS>2.0.ZU;2-Y
Abstract
alpha -Sulfonyl benzylic carbanions, derived from ortho-halobenzyl sulfones 5 (Hal = Br, I), can be easily generated by the phosphazene base P-2-Et an d react with different electrophiles such as alkyl halides, aldehydes and e thyl acrylate. Palladium catalysed cross-coupling reactions performed at th e halogen atom, followed by P-2-Et-mediated alkylation-dehydrosulfinylation process using bromoacetates as electrophiles allow the preparation of orth o-substituted cinnamates.