Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 18, Pages 10211-10218Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202100049
Keywords
C− F bond cleavage; gem-disilylated alkenes; high selectivity; iron catalysis
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Funding
- NSFC [21801029, 21890722, 21950410519]
- Fundamental Research Funds for the Central Universities [2020CDJQY-A043]
- Sichuan Key Laboratory of Medical Imaging (North Sichuan Medical College) [SKLMI201901]
- Nanchong City [19SXHZ0441, 19SXHZ0227]
- North Sichuan Medical College [19SXHZ0441, 19SXHZ0227]
- Chongqing Postdoctoral Science Foundation [cstc2019jcyj-bshx0057]
- China Postdoctoral Science Foundation [2020M673121]
- Natural Science Foundation of Chongqing [cstc2019jcyj-msxmX0048]
- Natural Science Foundation of Sichuan [2021YJ0413]
- Natural Science Foundation of Tianjin City [19JCJQJC62300, 18JCYBJC21400]
- Tianjin Research Innovation Project for Postgraduate Students [2019YJSB081]
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The iron-catalyzed defluorosilylation reaction is an efficient, highly functional-group compatible, and stereo- and regioselective reaction that can be used for late-stage silylation of biologically relevant compounds, offering opportunities for applications in medicinal chemistry.
The first iron-catalyzed defluorosilylation of unactivated gem-difluoroalkenes was developed, delivering gem-disilylated alkenes and (E)-silylated alkenes with excellent efficiency. This protocol features good functional group compatibility and excellent regio- and stereoselectivity, enabling the late-stage silylation of biologically relevant compounds, thus providing good opportunities for applications in medicinal chemistry. Preliminary mechanistic studies and DFT calculations reveal that a nucleophilic addition and elimination of the second C-F bond might be involved in the disilylation catalytic system, demonstrating unusual reactivity characteristics of iron catalysis.
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