Nucleophilic difluoromethylenation of aldehydes and ketones using diethyl difluoro(trimethylsilyl)methylphosphonate

Direct nucleophilic introduction of CF 2 group to aldehydes and ketones starting from diethyl difluoro(trimethylsilyl)methylphosphonate was achieved. Phosphates of syn and anti 2,2-difluoro-1,3-diols were produced in one reaction sequence and under mild conditions using catalytic amount of fluoride...

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Bibliographic Details
Published in:Journal of fluorine chemistry 2009-05, Vol.130 (5), p.493-500
Main Authors: Alexandrova, Anastasia V., Beier, Petr
Format: Article
Language:English
Subjects:
Difluoromethylenation
Nucleophilic addition
Phosphates
Phosphonates
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Summary:Direct nucleophilic introduction of CF 2 group to aldehydes and ketones starting from diethyl difluoro(trimethylsilyl)methylphosphonate was achieved. Phosphates of syn and anti 2,2-difluoro-1,3-diols were produced in one reaction sequence and under mild conditions using catalytic amount of fluoride initiator. A new nucleophilic difluoromethylenation of aldehydes and ketones using diethyl difluoro(trimethylsilyl)methylphosphonate ( 1) has been achieved. The reactive carbanion species were generated under mild reaction conditions with a catalytic amount of initiator. This methodology was compatible with non-enolizable and in some cases with enolizable aldehydes and ketones and provided a straightforward access to phosphates of syn and anti 2,2-difluoro-1,3-diols.
ISSN:0022-1139
1873-3328
DOI:10.1016/j.jfluchem.2009.02.015