Palladium(II)-Catalyzed [2+2+1] Annulation of Alkynes and Hydroxylamines: A Rodox-Neutral Approach to Fully Substituted Pyrroles
2022; American Chemical Society; Volume: 24; Issue: 28 Linguagem: Inglês
10.1021/acs.orglett.2c01925
ISSN1523-7060
AutoresJiaxing Bai, Nengni Xu, Hui Wang, Xinjun Luan,
Tópico(s)Synthesis and Characterization of Pyrroles
ResumoA palladium-catalyzed [2+2+1] annulation of alkynes and hydroxylamines has been developed for the rapid construction of fully substituted pyrroles. This transformation involves sequential nucleophilic-addition of hydroxylamine to alkyne, alkyne migratory insertion, and synergistic demetallization cyclization, which provides a redox-neutral annulation approach to pyrrole derivatives. Moreover, the strategy enabled alteration of the photophysical properties of pyrrole products by varying the aryl substituents, thus leading to the development of N-functionalized tetraarylpyrroles as new fluorophores.
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