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New Synthetic Methods
We have long-standing interests in the chemistry of heteroatom-substituted alkynes and alkenes, in particular ynamides and their derivatives. The synthesis of ynamides can often be limited in the scope of the nitrogen and carbon substituents, and to address this we developed a scalable route to ynamides from dichoroenamides, which are readily accessed from the reaction of an amide with trichloroethene under basic conditions. This method overcomes many traditional limitations, such as the use of carbamates, ureas, and aryl sulfonamides.
Chem. Commun., 2015,51, 3316-3319
We extended these studies to realise the first synthesis of yndiamides– alkynes with nitrogen atoms at both ends of the alkyne. Here we used a copper catalyzed coupling of dibromoenamides with amide nucleophiles to form yndiamides under mild conditions.
Angew. Chem. Int. Ed. 2017, 56, 14428.
These interesting alkynes are typically bench-stable, crystalline solids. These novel motifs underwent a wide range of transformations, including accessing a variety of doubly-aminated heterocycles, formation of novel fused pyrroles with extensive substitution, and gold-catalysed oxidative functionalizations to form unnatural amino acid derivatives.
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