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Conversion of Methyl Ketones and Methyl Sulfones into ?-Deutero-?,?-Difluoromethyl Ketones and ?-Deutero-?,?-Difluoromethyl Sulfones in Three Synthetic Steps.

ABSTRACT: Deuterodifluoromethyl ketones and sulfones were assembled in three synthetic steps from methyl ketones and sulfones, respectively. The key synthetic transformation is the deuteration of the difluorocarbanion generated by the release of trifluoroacetate from highly ?-fluorinated gem-diols. High levels of deuterium on the "CF2D" group were routinely observed. This strategy is mild and versatile and it can be applied to both ketones and sulfones without additional concerns of over- or under-fluorination. Additional examples address issues of over-deuteration when compounds with other acidic protons are subjected to the reaction conditions. This process not only demonstrates a new method to install a "CF2D" group but also extends the scope of trifluoroacetate release to sulfones.

SUBMITTER: Sowaileh MF

PROVIDER: S-EPMC5608106 | biostudies-literature | 2017 Feb

REPOSITORIES: biostudies-literature

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Conversion of Methyl Ketones and Methyl Sulfones into α-Deutero-α,α-Difluoromethyl Ketones and α-Deutero-α,α-Difluoromethyl Sulfones in Three Synthetic Steps.

Sowaileh Munia F MF Han Changho C Hazlitt Robert A RA Kim Eun Hoo EH John Jinu P JP Colby David A DA

Tetrahedron letters 20161221 5

Deuterodifluoromethyl ketones and sulfones were assembled in three synthetic steps from methyl ketones and sulfones, respectively. The key synthetic transformation is the deuteration of the difluorocarbanion generated by the release of trifluoroacetate from highly α-fluorinated gem-diols. High levels of deuterium on the "CF<sub>2</sub>D" group were routinely observed. This strategy is mild and versatile and it can be applied to both ketones and sulfones without additional concerns of over- or un ...[more]

PMID: 28943667

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