130156-55-7Relevant academic research and scientific papers
Atom Efficient Synthesis of Selectively Difluorinated Carbocycles through a Gold(I)-Catalyzed Cyclization
McCarter, Adam W.,Sommer, Magdalena,Percy, Jonathan M.,Jamieson, Craig,Kennedy, Alan R.,Hirst, David J.
, p. 8888 - 8905 (2018)
The intramolecular carbocyclization of difluorinated enol acetals has been achieved for the first time using gold(I) catalysis. Difluorinated enol acetals bearing a pendant alkene group can be cyclized and reduced in one pot to form fluorinated diol motifs. Alternatively, the cyclization of terminal alkynes allows for the synthesis of fluorinated pyran scaffolds. Both cyclization processes can be performed under mild conditions allowing access to complex products rich in functionality. The cyclic systems are synthesized concisely (maximum four steps) from trifluoroethanol, an inexpensive fluorinated feedstock.
Chelated [3,3]-rearrangements of difluoroallylic alcohols
Broadhurst,Percy,Prime
, p. 5903 - 5906 (2007/10/03)
Whereas the lithium enolates of acetate and propionate esters of difluoroallylic alcohols fragment rapidly, even at -78*C, methoxy- and benzyloxy-acetates form chelated enolates which undergo smooth [3,3]-rearrangement as their silyl ketene acetals. The latent ketone function can be revealed under mild conditions CMeOH,SOCl2) to afford very highly functionalised CF2 compounds.
New Fluorine-containing Building Blocks from Trifluoroethanol. 1.
Patel, Sunita T.,Percy, Jonathan M.,Wilkes, Robin D.
, p. 9201 - 9216 (2007/10/02)
A new fluorine containing acyl anion equivalent 1,1-difluoro-2-lithio-2-ethene 12 has been prepared from trifluoroethanol and trapped with a number of electrophiles in good yield.Effective electrophiles included Group(IV) halides a
