Experiment and Computational Study on Pd‐Catalyzed MIA‐Directed Ortho‐C−H Alkynlation of Phenylalanine

The direct ortho‐alkynylation of substituted phenylalanine has been successfully achieved through methoxyiminoacyl (MIA)‐mediated Pd‐catalyzed C−H functionalization. This innovative protocol showcases the ability to apply a diverse range of phenylalanine substrates, resulting in the efficient synthe...

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Bibliographic Details
Published in:Asian journal of organic chemistry 2024-07, Vol.13 (7), p.n/a
Main Authors: Zhang, Fujie, Liang, Yu, Liu, Dong‐Hui, Liu, Peng‐Yu, Huang, Liangliang, He, Yu‐Peng, Yu, Fang
Format: Article
Language:English
Subjects:
alkynlation
Chemical synthesis
C−H activation
Electropositivity
MIA
Phenylalanine
Substrates
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Summary:The direct ortho‐alkynylation of substituted phenylalanine has been successfully achieved through methoxyiminoacyl (MIA)‐mediated Pd‐catalyzed C−H functionalization. This innovative protocol showcases the ability to apply a diverse range of phenylalanine substrates, resulting in the efficient synthesis of alkynylation benzylamine derivatives with notable effectiveness. Computational investigations further revealed that the fluoride ion enhances the electropositivity of Pd(IV) and the interaction between C1 and C2 within the transition state of the reductive elimination, which significantly expedites the reductive elimination step in the alkynylation process. A highly efficient MIA‐mediated C(sp2)−H alkynylation of amides, which tolerates various substituent groups with good to high yields. This method features high efficiency and wide functional group tolerance.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.202400159