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Costa A, Nájera C, Sansano JM. Synthetic applications of o- and p-halobenzyl sulfones as zwitterionic synthons: preparation of ortho-substituted cinnamates and biarylacetic acids. J Org Chem. 2002;67(15):5216-25doi: 10.1021/jo025620s.
Costa, A., Nájera, C., & Sansano, J. M. (2002). Synthetic applications of o- and p-halobenzyl sulfones as zwitterionic synthons: preparation of ortho-substituted cinnamates and biarylacetic acids. The Journal of organic chemistry, 67(15), 5216-25. https://doi.org/10.1021/jo025620s
Costa, Ana, et al. "Synthetic applications of o- and p-halobenzyl sulfones as zwitterionic synthons: preparation of ortho-substituted cinnamates and biarylacetic acids." The Journal of organic chemistry vol. 67,15 (2002): 5216-25. doi: https://doi.org/10.1021/jo025620s
Costa A, Nájera C, Sansano JM. Synthetic applications of o- and p-halobenzyl sulfones as zwitterionic synthons: preparation of ortho-substituted cinnamates and biarylacetic acids. J Org Chem. 2002 Jul 26;67(15):5216-25. doi: 10.1021/jo025620s. PMID: 12126409.
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J Org Chem. 2002 Jul 26;67(15):5216-25. doi: 10.1021/jo025620s.

Synthetic applications of o- and p-halobenzyl sulfones as zwitterionic synthons: preparation of ortho-substituted cinnamates and biarylacetic acids.

The Journal of organic chemistry

Ana Costa, Carmen Nájera, José M Sansano

Affiliations

  1. Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Alicante, E-03080 Alicante, Spain.

PMID: 12126409 DOI: 10.1021/jo025620s

Abstract

The synthetic applications of o-halobenzyl and p-halobenzyl sulfones as precursors of 1,3- and 1,5-zwitterionic synthons, respectively, are described. Their alpha-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.

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