Amines are critical functional groups that are incorporated into many biologically active compounds and functional materials of importance to the biomedical, agrochemical and fine-chemical industries. An idealized synthetic approach for the preparation of this important class of compounds would take advantage of the direct and byproduct free conversion of feedstock alkenes directly into unprotected amines with good regio- and stereoselectivity under mild reaction conditions. These goals could be realized with early transition metal catalyzed hydroaminoalkylation (Scheme 1), a C—H functionalization reaction a to nitrogen that results in selective C—C bond formation. However, to date, all promising Group 4 and 5 metal complexes for this transformation demand harsh reaction conditions. The identification of a system that can be used with mild reaction conditions is desirable. Here we show that by using a sterically demanding, N,O-chelating, electron-withdrawing phosphoramidate as an easily installed auxiliary ligand, room-temperature alkene hydroaminoalkylation can be achieved for the first time.
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