Isoxazoles as efficient alkyne amination reagents in divergent heterocycle synthesis

During the past decades, the exploration of new alkyne amination reactions has attracted increasing attention due to the high efficiency in heterocycle synthesis. In addition to the well-established alkyne amination reagents (such as nitrogen ylides and azides), isoxazoles and their derivatives have been proven to be efficient amination reagents, especially the N,O-bifunctional reagents of alkynes, in the transition metal-catalyzed transformation of alkynes through metal carbene intermediates. Isoxazole derivatives have been extensively applied to the rapid synthesis of a diverse range of structurally complex N-containing molecules, especially the valuable N-heterocycles in atom-economic manner. In this review, we summarize the latest trends and developments of isoxazole-enabled alkyne amination reactions and their applications in divergent heterocycle synthesis, including amination of ynamides, amination of ynol ethers, amination of thioynol ethers, amination of electron-deficient alkynes, amination of unpolarized alkynes and asymmetric amination of alkynes. Finally, we list the current challenges and opportunities for potential breakthroughs in this field.