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Metal-Free Multifunctionalization of Alkynes Promoted by Acid and Selectfluor
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DOI：10.1002/ajoc.70447.png)
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Abstract
En 中文
Herein, we describe a metal-free approach for the tetrafunctionalization of internal alkynes using an acid/Selectfluor system. This method efficiently forms four new chemical bonds (C─F, C─C, and C─N) in a single step, enabling the construction of amide-containing fluorene under mild conditions. The reaction proceeds through a carbocation-based mechanism initiated by 1,6-enyne cyclization, with acetonitrile serving as both solvent and the amide source. Gram-scale synthesis demonstrates the practical utility of this transformation, while mechanistic studies verify the origin of the amide group and the involvement of a deuterium kinetic isotope effect (DKIE). This work establishes a distinct, transition-metal-free pathway for alkyne multifunctionalization, offering a complementary strategy to existing synthetic methods.
Keywords:
1,6-alkynes
metal-free
multifunctionalization
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