Amidomercuriation: a general addition of amides and related compounds to olefins

Abstract

The addition of different carboxamides and related compounds such as urethane or urea to olefins using mercury (II) nitrate followed by sodium borohydride reduction to give the corresponding N-substituted amides, urethanes, or ureas, respectively, is described. The monoalkylated ureas, through the same amidomercuriation–demercuriation procedure, yield symmetrical and unsymmetrical N,N′-disubstituted ureas. This amidomercuriation–demercuriation process provides a new, convenient, and general method for the Markovnikov amidation of carbon–carbon double bonds.