104483-68-3

Upstream product

• 75-97-8 3,3-dimethyl-butan-2-one 
• 444-29-1 2-iodo(trifluoromethyl)benzene 
• 88-16-4 1-chloro-2-(trifluoromethyl)benzene 

Relevant academic research and scientific papers

Palladium-catalyzed α-ketone arylation under mild conditions

The α-arylation of ketones with aryl halides catalyzed by the easily prepared and air-stable palladium complex (SIPr)Pd(Py)Cl2 (3) is described. Complex 3 displays high activity for a variety of aryl halides (activated, unactivated, and sterically hindered aryl halides) under mild conditions. Moreover, both aryl and alkyl ketones can be arylated. The α-arylation of some alkyl ketones can even be run at room temperature. The mono- or diarylated products of the unhindered dialkyl ketone 3-pentanone could be controlled by temperature and the ratio of ketones to aryl halides. Palladium-catalyzed α-ketone arylation of aryl and alkyl ketones with aryl halides is described. A total of 31 examples is presented with yields ranging from 45 to 95%.The mono- or diarylated product of the unhindered dialkyl ketone 3-pentanone could be controlled. Copyright

The Peculiar Behaviour of the Trifluoromethyl Substituent in SRN1 Processes

Reaction of the enolate of 3,3-dimethylbutan-2-one with α,α,α-trifluoro-o-iodotoluene in a SRN1 process does not yield the excepted substitution product, but a more complex molecule deriving from it.An accurate n.m.r. analysis of the products, along with other evidence, indicates a mechanism for this rearrangement, where an interaction of the trifluoromethyl group with the adjacent enolate moiety occurs, once the 'normal' SRN1 substitution product has formed.The peculiar effect of the CF3 substituent is not only confined to the ortho position.Even α,α,α-trifluoro-p-iodotoluene shows unusual behaviour and affords a rearranged product.A mechanistic explanation is offered, where some of the key steps are similar to those involved in the case of the ortho isomer.