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Base Catalysis Enables Access to ?,?-Difluoroalkylthioethers.

ABSTRACT: A nucleophilic addition reaction of aryl thiols to readily available ?,?-difluorostyrenes provides ?,?-difluoroalkylthioethers. The reaction proceeds through an unstable anionic intermediate, prone to eliminate fluoride and generate ?-fluorovinylthioethers. However, the use of base catalysis overcomes the facile ?-fluoride elimination, generating ?,?-difluoroalkylthioethers in excellent yields and selectivities.

SUBMITTER: Orsi DL

PROVIDER: S-EPMC5485667 | biostudies-literature | 2017 Apr

REPOSITORIES: biostudies-literature

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Base Catalysis Enables Access to α,α-Difluoroalkylthioethers.

Orsi Douglas L DL Easley Brandon J BJ Lick Ashley M AM Altman Ryan A RA

Organic letters 20170323 7

A nucleophilic addition reaction of aryl thiols to readily available β,β-difluorostyrenes provides α,α-difluoroalkylthioethers. The reaction proceeds through an unstable anionic intermediate, prone to eliminate fluoride and generate α-fluorovinylthioethers. However, the use of base catalysis overcomes the facile β-fluoride elimination, generating α,α-difluoroalkylthioethers in excellent yields and selectivities. ...[more]

PMID: 28332397

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