Silver catalyzed zinc Barbier reaction of benzylic halides in water

Benzylic chlorides react in aqueous dibasic potassium phosphate under silver catalysis with aromatic aldehydes in the presence of zinc dust to give 1,2-diaryl alcohols in moderate to good yields. Dimerization to bibenzyls and reduction of the halide are important side reactions. A wide range of subs...

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Bibliographic Details
Published inTetrahedron letters Vol. 39; no. 51; pp. 9393 - 9396
Main Authors Bieber, Lothar W., Storch, Elisabeth C., Malvestiti, Ivani, da Silva, Margarete F.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 17.12.1998
Elsevier
Subjects
addition
Barbier reaction
Chemistry
Chemistry, Organic
dimerization
Physical Sciences
reduction
Science & Technology
silver catalysis
dimerization
silver catalysis
reduction
Barbier reaction
addition
ORGANIC-SYNTHESIS
KETONES
AQUEOUS-MEDIA
ALLYLATION
METALLIC TIN
ALDEHYDES
ADDITIONS
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Summary:Benzylic chlorides react in aqueous dibasic potassium phosphate under silver catalysis with aromatic aldehydes in the presence of zinc dust to give 1,2-diaryl alcohols in moderate to good yields. Dimerization to bibenzyls and reduction of the halide are important side reactions. A wide range of substituted aromatic and heteroaromatic aldehydes and of substituted benzylic chlorides can be used. Aliphatic aldehydes and ketones are unreactive. A mechanism of two SET on the metal surface is discussed. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(98)02199-6