Iron-Catalyzed Tunable Alkene Migratory Silylation and Transposition

The example of iron-catalyzed alkenes migratory silylation and transposition has been demonstrated, affording a tunable approach to synthesize thermodynamically stable allylsilanes and internal alkenes with high efficiency and regioselectivity. These reactions showcase several advantageous features, including good functional group tolerance, excellent regioselectivity, a broad substrate scope, scalability to gram-scale synthesis, and late-stage functionalization of bio-relevant molecules. Furthermore, the relay catalytic mechanism of the migratory silylation, involving both iron-silyl and iron-hydride intermediates, provides valuable insights into iron-catalyzed coupling reactions, opening new avenues for the development of novel transformations under iron catalysis.

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Publication Details

Journal
Organic Letters
Published
2025-05-09
DOI
https://doi.org/10.1021/acs.orglett.5c01273
Citations
2
Primary Topic
Asymmetric Hydrogenation and Catalysis
Type
article
Field-Weighted Citation Impact
1.07

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article

Iron-Catalyzed Tunable Alkene Migratory Silylation and Transposition

Hong Huang, Ruichen Zhang, Feng Zhang, Chang Qiao et al.
2 citations
Organic Letters
Asymmetric Hydrogenation and Catalysis
1.07
article

Iron-Catalyzed Tunable Alkene Migratory Silylation and Transposition

Hong Huang, Ruichen Zhang, Feng Zhang, Chang Qiao, Shasha Geng, Yu Pu, Bohao Guo, Qing‐Yun Wu
article en
2 citations

Abstract

The example of iron-catalyzed alkenes migratory silylation and transposition has been demonstrated, affording a tunable approach to synthesize thermodynamically stable allylsilanes and internal alkenes with high efficiency and regioselectivity. These reactions showcase several advantageous features, including good functional group tolerance, excellent regioselectivity, a broad substrate scope, scalability to gram-scale synthesis, and late-stage functionalization of bio-relevant molecules. Furthermore, the relay catalytic mechanism of the migratory silylation, involving both iron-silyl and iron-hydride intermediates, provides valuable insights into iron-catalyzed coupling reactions, opening new avenues for the development of novel transformations under iron catalysis.

Organic LettersVol. 27(20)
North Sichuan Medical University (CN), Chongqing University (CN), Chemical Synthesis Lab (SG)
National Natural Science Foundation of China, Fundamental Research Funds for the Central Universities
Openalex Percentile: Top 24%
Asymmetric Hydrogenation and Catalysis
1.07
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