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N-Silylenamines as Reactive Intermediates: Hydroamination for the Modular Synthesis of Selectively Substituted Pyridines

Erica K. J. Lui, Daniel Hergesell, Laurel L. Schafer*

*Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, British Columbia, Canada V6T 1Z1, Email: schaferchem.ubc.ca

E. K. J. Lui, D. Hergesell, L. L. Schafer, Org. Lett., 2018, 20, 6663-6667.

DOI: 10.1021/acs.orglett.8b02703 (free Supporting Information)



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Abstract

Regioselective hydroamination of alkynes with N-silylamine using a bis(amidate)bis(amido)titanium(IV) precatalyst, addition of α,β-unsaturated carbonyls to the crude mixture followed by oxidation affords 47 examples of pyridines in good yields containing variable substitution patterns, including pharmaceutically relevant 2,4,5-trisubstituted pyridines.


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Key Words

pyridines, DDQ


ID: J54-Y2018