REACTION OF ORGANOBORANES WITH LEAD(IV) ACETATE AZIDE. A SYNTHESIS OF AZIDOALKANES FROM ALKENES VIA HYDROBORATION.

Article abstract of DOI:10.1246/bcsj.57.1026

Trialkylboranes prepared from alkenes via hydroboration react with lead(IV) acetate azide in dichloromethane at minus 25 degree C to form the corresponding azidoalkanes in a one-pot manner. One of two of the alkyl groups of trialkylboranes are utilized in the reaction. For example, 1-azidohexane is afforded from 1-hexene in 50% yield based on the alkene employed.