Title of article
Acylation of α-(N-carbamoyl)alkylcuprates and alkyl- or aryl(halo)cuprates
Author/Authors
R.Karl Dieter، نويسنده , , Ram R. Sharma، نويسنده , , Huayun Yu، نويسنده , , Vinayak K. Gore، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2003
Pages
12
From page
1083
To page
1094
Abstract
α-(N-Carbamoyl)alkylcuprates [R2CuLi·LiX or RCuXLi (X=CN, Cl)] when prepared from THF soluble CuX·2LiCl (X=Cl, CN) undergo a reliable and generally high yield reaction with aroyl, alkanoyl, and alkenoyl chlorides to provide a rapid and efficient synthesis of α-carbamoyl ketones. Cuprates prepared from acyclic, cyclic, and a functionalized carbamate can be utilized. Although yields are a function of cuprate reagent and substrate structure, nearly quantitative yields can be obtained with reagents generated from 2RLi+CuCN·2LiCl. The use of reagents generated from CuCl·2LiCl are more efficient in the α-(N-carbamoyl)alkyl ligand, although yields are slightly lower. Acylation of alkyl(chloro)cuprates generated from one equivalent of CuCl·2LiCl and organolithium or Grignard reagents provides an efficient and high yield procedure for ketone synthesis.
Keywords
Acylation , Deprotonation , aryl cuprates , ?-(N-carbamoyl)alkylcuprates
Journal title
Tetrahedron
Serial Year
2003
Journal title
Tetrahedron
Record number
1087521
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