124050-66-4Relevant academic research and scientific papers
Catalytic Domino Reaction of Ketones/Aldehydes with Me3SiCF2Br for the Synthesis of α-Fluoroenones/α-Fluoroenals
Song, Xiaoning,Chang, Jian,Zhu, Dongsheng,Li, Jiaheng,Xu, Cong,Liu, Qun,Wang, Mang
supporting information, p. 1712 - 1715 (2015/04/14)
A unique domino reaction of enolizable carbonyl compounds with Me3SiCF2Br to construct α-fluoroenones and α-fluoroenals is described to undergo the in situ formation of difluorocarbene and silyl enol ether, difluorocyclopropanation, desilylation, ring-opening, and defluorination sequence. In this tandem reaction, Me3SiCF2Br acts as not only the difluorocarbene source but also the TMS transfer agent as well as internal bromide and fluoride anion catalyst. It allows the transformations to occur smoothly under only a catalytic amount of n-Bu4NBr as initiator.
First stereospecific synthesis of (E)- or (Z)-α-fluoroenones via a kinetically controlled Negishi coupling reaction
Dutheuil, Guillaume,Paturel, Clotilde,Lei, Xinsheng,Couve-Bonnaire, Samuel,Pannecoucke, Xavier
, p. 4316 - 4319 (2007/10/03)
A highly stereospecific synthesis of (E)- or (Z)-α-fluoro-α, β-unsaturated ketones 4, via a kinetically controlled Negishi palladium-catalyzed coupling reaction, was developed, providing an easy and general access to valuable fluorinated intermediates (pharmaceutical, peptide mimic, and so on). The synthesis involved a reaction between E/Z gem-bromofluoroolefins 2 and alkoxyvinylzinc species 6 under controlled reaction temperature. At 10 °C, (Z)-4 (70 to 99% yields) was obtained along with unreacted (Z)-2 (66 to 99% yields). At THF reflux, the recovered olefin was transformed into (E)-4 (up to 98% yield).
A general and efficient synthesis of β-ketophosphonates
Coutrot, Philippe,Grison, Claude,Lachgar, Mohamed,Ghribi, Abdelaziz
, p. 925 - 942 (2007/10/02)
The acylation of organocuprates or organolithiated reagents with 2-dialkylphosphonoalkanoyl chlorides or dialkylphosphonofluoroacetyl chlorides represents a general and efficient route to β-ketophosphonates.A Horner reaction between the lithiated anions derived from α-fluoro-β-ketophosphonates and aldehydes leads to 2-fluoro-2-enones whereas the lithiated anions derived from γ-acetylenic-β-ketophosphonates afford enynones. β-ketophosphonate / 2-dialkylphosphonoalkanoyl chloride / dialkylphosphonofluoroacetyl chloride / 2-fluoro-2-enone / enynone
SYNTHESE GENERALE DE β-CETOPHOSPHONATES α-FLUORES PRECURSEURS D'ENONES α-FLUOREES, APPLICATION EN SERIE PYRETHRENIQUE.
Coutrot, Ph.,Grison, C.
, p. 2655 - 2658 (2007/10/02)
Dialkylphosphonoflouracetylchlorides are used to introduce directly the 2-oxophosphonate 1-fluorinated synthons on organometallic reagents.A Horner reaction of the 3 derivated anions with aldehydes gave various 2-fluoro-2-enones.Application to the cis, trans caronaldehyde ethyl ester led to the 2-fluoroethenyl pyrethroid derivatives.
