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Lewis acid-promoted hydrofluorination of alkynyl sulfides to generate ?-fluorovinyl thioethers.

ABSTRACT: A new method for the preparation of ?-fluorovinyl thioethers is reported which involves the hydrofluorination of alkynyl sulfides with 3HF·Et3N, a process that requires Lewis acid activation using BF3·Et2O and TiF4. The method gives access to a range of ?-fluorovinyl thioethers, some in high stereoselectivity with the Z-isomer predominating over the E-isomer. The ?-fluorovinyl thioether motif has prospects as a steric and electronic mimetic of thioester enols and enolates, important intermediates in enzymatic C-C bond forming reactions. The method opens access to appropriate analogues for investigations in this direction.

SUBMITTER: Bello D

PROVIDER: S-EPMC4661019 | biostudies-literature | 2015

REPOSITORIES: biostudies-literature

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Lewis acid-promoted hydrofluorination of alkynyl sulfides to generate α-fluorovinyl thioethers.

Bello Davide D O'Hagan David D

Beilstein journal of organic chemistry 20151014

A new method for the preparation of α-fluorovinyl thioethers is reported which involves the hydrofluorination of alkynyl sulfides with 3HF·Et3N, a process that requires Lewis acid activation using BF3·Et2O and TiF4. The method gives access to a range of α-fluorovinyl thioethers, some in high stereoselectivity with the Z-isomer predominating over the E-isomer. The α-fluorovinyl thioether motif has prospects as a steric and electronic mimetic of thioester enols and enolates, important intermediate ...[more]

PMID: 26664609

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