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Updated: Feb 3, 2026

Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates
Published on: March 6, 2019
N-Silylenamines as Reactive Intermediates: Hydroamination for the Modular Synthesis of Selectively Substituted
Erica K J Lui1, Daniel Hergesell1, Laurel L Schafer1
1Department of Chemistry , University of British Columbia , 2036 Main Mall , Vancouver , British Columbia , Canada V6T 1Z1.
Abstract:
A modular and selective synthesis of mono-, di-, tri-, tetra-, and pentasubstituted pyridines is reported. Hydroamination of alkynes with N-silylamine using a bis(amidate)bis(amido)titanium(IV) precatalyst furnishes the regioselective formation of N-silylenamines. Addition of α,β-unsaturated carbonyls to the crude mixtures followed by oxidation affords 47 examples of pyridines in yields of up to 96%. This synthetic route allows for the synthesis of diverse pyridines containing variable substitution patterns, including pharmaceutically relevant 2,4,5-trisubstituted pyridines, using this one-pot protocol.
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