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.

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