American Chemical Society
ja7b13783_si_003.cif (1.73 MB)

Regio- and Stereoselective Hydroamination of Alkynes Using an Ammonia Surrogate: Synthesis of N‑Silylenamines as Reactive Synthons

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posted on 2018-03-12, 00:00 authored by Erica K. J. Lui, Jason W. Brandt, Laurel L. Schafer
An anti-Markovnikov selective hydroamination of alkynes with N-silylamines to afford N-silylenamines is reported. The reaction is catalyzed by a bis­(amidate)­bis­(amido)­Ti­(IV) catalyst and is compatible with a variety of terminal and internal alkynes. Stoichiometric mechanistic studies were also performed. This method easily affords interesting N-silylenamine synthons in good to excellent yields and the easily removable silyl protecting group enables the catalytic synthesis of primary amines.