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Successive C-C bond cleavage, fluorination, trifluoromethylthio- and pentafluorophenylthiolation under metal-free conditions to provide compounds with dual fluoro-functionalization.

ABSTRACT: The selective C-C bond cleavage and simultaneous formation of two C-F bonds and one C-S bond in ?-keto esters with nucleophilic fluorination reagents such as DAST under metal-free/catalyst-free conditions is disclosed. Double fluorination at two remote carbons with additional dialkylamino-sulfenylation provided unique fluorinated compounds in good to high yields. This method can be applied for the successive C-C bond cleavage/fluorination/trifluoromethylthiolation of ?-keto esters using trifluoromethyl-DAST (CF3-DAST) providing different type of fluorinated and trifluoromethylthiolated compounds via a shunt pathway. Doubly fluoro-functionalized compounds obtained in these reactions are unique and difficult to synthesize by other methods.

SUBMITTER: Saidalimu I

PROVIDER: S-EPMC5968529 | biostudies-literature | 2016 Mar

REPOSITORIES: biostudies-literature

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Successive C-C bond cleavage, fluorination, trifluoromethylthio- and pentafluorophenylthiolation under metal-free conditions to provide compounds with dual fluoro-functionalization.

Saidalimu Ibrayim I Suzuki Shugo S Tokunaga Etsuko E Shibata Norio N

Chemical science 20151209 3

The selective C-C bond cleavage and simultaneous formation of two C-F bonds and one C-S bond in β-keto esters with nucleophilic fluorination reagents such as DAST under metal-free/catalyst-free conditions is disclosed. Double fluorination at two remote carbons with additional dialkylamino-sulfenylation provided unique fluorinated compounds in good to high yields. This method can be applied for the successive C-C bond cleavage/fluorination/trifluoromethylthiolation of β-keto esters using trifluor ...[more]

PMID: 29899937

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