A New and Facile Method for Stereoselective Synthesis of (E)-Styryl Bromides by the Reduction of 1,1-Dibromoalkenes Using LiAlH₄-EtOAc (1:1)

Abstract

A facile method for stereoselective synthesis of (E)-styryl bromides by the reduction of 1,1-dibromoalkenes using LiAlH₄-EtOAc (1:1) is described. We believe that the present procedure is a good alternative to the Tokuda’s microwave method with good stereoselectivity.

Key words

1,1-dibromoalkenes - LiAlH₄-EtOAc - styryl bromides

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14

The use of other reagents, such as Li(i-Bu)₂BuAlH, LiEt₃BH and Li(s-Bu)₃BH, gave less satisfactory results. In the case of NaBH₄, no reaction occurred.

15

When the reaction time was made longer from 2 h to 7 h, an increase in the ratio of the styrene was observed as shown below (Scheme [1] ).

 

Scheme 1