Journal
ORGANIC LETTERS
Volume 24, Issue 28, Pages 5099-5104Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c01925
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Funding
- National Natural Science Foundation of China [21925108]
- Science and Technology of Shaanxi Province [2022JM-084]
- Tangfoundation of Northwest University [360151900004]
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A palladium-catalyzed [2+2+1] annulation of alkynes and hydroxylamines has been developed for the rapid construction of fully substituted pyrroles. This strategy enabled alteration of the photophysical properties of pyrrole products by varying the aryl substituents, leading to the development of N-functionalized tetraarylpyrroles as new fluorophores.
A 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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