Bromination/desilicobromination of silylated monofluoroalkenes using tetrabutylammonium tribromide under microwave conditions

New conditions for the bromination/desilicobromination of silylated monofluoroalkenes using tetrabutylammonium tribromide under microwave conditions are presented. The reaction is fast (20 min) and provide, after the desilicobromination step, the bromofluoroalkene where the replacement of the silyl group is done with retention of configuration with little or no stereochemical erosion. Isomeric enrichment is even observed in one case. Optimization of the reactions conditions and applications to various substrates are reported.

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► Bromination/desilicobromination of silylated monofluoroalkenes was achieved.
► New conditions use tetrabutylammonium tribromide under microwave irradiations.
► Little or no stereochemical erosion is observed for the substitution of the silyl group.