447464-51-9Relevant academic research and scientific papers
Synthetic applications of o- and p-halobenzyl sulfones as zwitterionic synthons: Preparation of Ortho-substituted cinnamates and biarylacetic acids
Costa, Ana,Najera, Carmen,Sansano, Jose M.
, p. 5216 - 5225 (2007/10/03)
The synthetic applications of o-halobenzyl and p-halobenzyl sulfones as precursors of 1,3- and 1,5-zwitterionic synthons, respectively, are described. Their α-sulfonyl carbanions, generated by means of the phosphazene base P2-Et or BuLi or K2CO3 under PTC conditions, reacted with different electrophiles such as alkyl halides, aldehydes, and electrophilic olefins. Palladium-catalyzed cross-coupling processes such as Heck, Suzuki, and Sonogashira reactions can be efficiently performed at the halogen atom. These two sequential functionalization processes are applied to the synthesis of ortho-substituted cinnamates and pharmaceuticals belonging to the family of p-biarylacetic acids such as 4-biphenylacetic acid, namoxyrate, xenyhexenic acid, and biphenylpropionic acid.
P2-Et-mediated deprotonation of ortho-halobenzyl sulfones: Synthetic applications as zwitterionic synthons
Costa,Nájera,Sansano
, p. 1881 - 1884 (2007/10/03)
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
