Lithium dialkylcuprates acylation

Like aldehydes, ketones can be prepared in a number of ways. The following sections detail some of the more common preparation methods the oxidation of secondary alcohols, the hydration of alkynes, the ozonolysis of alkenes, Friedel-Crafts acylation, the use of lithium dialkylcuprates, and the use of a Grignard reagent. 

The addition of a lithium dialkylcuprate (Gilman reagent) to an acyl chloride at low temperatures produces a ketone. This method produces a good yield of acetophenone. 

Acylation of Lithium Dialkylcuprates with Acid Chlorides or Thiol Esters... 

The use of the more reactive lithium dialkylcuprate (R2CuLi) species in acylation requires the complete exclusion of moisture and air. This fact makes application of organocuprate acylation early in a... 

Trialkylboranes are able to transfer an alkyl group onto l-acyl-2-vinylcyclopropanes with simultaneous opening of the ring. Since this reaction requires oxygen, a radical mechanism has been postulated. The yields of these reactions were too low for practical purposes however, this difficulty was overcome by the use of lithium dialkylcuprates rather than trialkylboranes as alkylating agents or by the use of copper(I) methyltrialkylborates, The reaction... 

Like selenol esters, tellurol esters can also serve as acyl transfer reagents, giving rise to the corresponding ketones, carboxylic acids, and esters. For example, tellurol esters react with lithium dialkylcuprates at -78 °C to give the corresponding ketones in high yields (Eq. 63) [117]. 

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