Abstract
A long-standing challenge in synthetic chemistry is the development of the transamidation reaction. This process, which involves the conversion of one amide to another, is typically plagued by unfavourable kinetic and thermodynamic factors. Although some advances have been made with regard to the transamidation of primary amide substrates, secondary amide transamidation has remained elusive. Here we present a simple two-step approach that allows for the elusive overall transformation to take place using non-precious metal catalysis. The methodology proceeds under exceptionally mild reaction conditions and is tolerant of amino-acid-derived nucleophiles. In addition to overcoming the classic problem of secondary amide transamidation, our studies expand the growing repertoire of new transformations mediated by base metal catalysis.
Highlights
A long-standing challenge in synthetic chemistry is the development of the transamidation reaction
Our studies commenced by surveying the reaction of simple benzamides and morpholine using nickel catalysis
No reaction takes place if the nickel and SIPr are excluded from the reaction, highlighting the unique ability of nickel catalysis to facilitate the net transamidation reaction
Summary
A long-standing challenge in synthetic chemistry is the development of the transamidation reaction. This process, which involves the conversion of one amide to another, is typically plagued by unfavourable kinetic and thermodynamic factors. Some advances have been made with regard to the transamidation of primary amide substrates, secondary amide transamidation has remained elusive. Two main challenges must be overcome to achieve the transamidation of secondary amides. The state-of-the-art methodology to achieve the transamidation of secondary amides gives equilibrium mixtures of substrate and product amides[10,12]. High kinetic barrier because of resonance stabilization of amide Unfavourable thermodynamics/thermoneutral process b Two-step approach to net transamidation of secondary amides
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