1,2-Aminofunctionalization Reactions of Pyridino-Alkynes via Carbophilic Activation

Chem Rec. 2021 Dec;21(12):3779-3794. doi: 10.1002/tcr.202100145. Epub 2021 Oct 20.

Abstract

Transition metal-catalyzed 1,2-difunctionalization reactions of alkynes have emerged as a powerful tool to forge carbon-carbon and carbon-heteroatom bonds for the rapid synthesis of polyfunctionalized molecular scaffolds. In this regard, our group has persistently been developing transition metal-mediated 1,2-aminofunctionalization reactions of alkynes through a rationally designed pyridino-alkyne core by utilizing the carbophilic activation strategy. In this account, we present an array of such 1,2-aminofunctionalization reactions which have been successfully executed on this core to afford important polycyclic frameworks such as functionalized quinalizinones, pyridinium oxazole dyads (PODs), N-doped polycyclic aromatic hydrocarbons (PAHs), N-doped spiro-PAHs. Additionally, the synthesis of phosphine ligated gold complexes bearing pyrido-isoquinoline scaffold from the pyridino-alkynes will be discussed briefly.

Keywords: 1,2-aminofunctionalization; carbophilic activation strategy; coinage metal catalysis; nitrogen-containing heterocycles; pyridino-alkynes.

Publication types

  • Review