Haloamines are highly conserved molecular scaffold among blockbuster drugs and natural products. Thus, there is a continuous demand for the development of more efficient and systematic methods for their synthesis. We have found that Iron (II) salts and hydroxylamine sulfonic acid under moderate heat promote the stereospecific haloamination of a variety of alkenes. These efforts have determined that fluoro-, chloro- and bromoaminations under those conditions efficiently provide the desired haloamines. The success of this novel method would provide access to potential novel asymmetric methods for the synthesis of such privileged scaffolds.

Studies towards the iron(II)-promoted stereoselective haloamination of alkenes

253rd National Meeting (2017)

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