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 inAsian journal of organic chemistry Vol. 13; no. 7
Main Authors Zhang, Fujie, Liang, Yu, Liu, Dong-Hui, Liu, Peng-Yu, Huang, Liangliang, He, Yu-Peng, Yu, Fang
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.07.2024
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
C-H activation
MIA
1,5-ENYNES
2+2+2 CYCLOADDITION
alkynlation
ALKYNYLATION
SELECTIVITY
CYCLIZATION
AMIDES
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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.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.202400159