Enantioselective domino alkyl arylation of vinyl phosphonates by combining photoredox and nickel catalysis Article Swipe
Tingzhi Lin
,
Guorong Li
,
Qianqian Lü
,
Chen Zhang
,
Yan‐En Wang
,
Fei Xing
,
Yundong Xu
,
Kun Yang
,
Dan Xiong
,
Xiufang Xu
,
Patrick J. Walsh
,
Jianyou Mao
·
YOU?
·
· 2024
· Open Access
·
· DOI: https://doi.org/10.1016/j.gresc.2024.04.001
YOU?
·
· 2024
· Open Access
·
· DOI: https://doi.org/10.1016/j.gresc.2024.04.001
A nickel/photoredox mediated asymmetric domino alkyl arylation of vinyl phosphonates to generate a diverse array of enantioenriched α-aryl phosphonates is disclosed. This asymmetric three-component difunctionalization couples aryl halides and alkyl bromides with vinyl phosphonates, exhibiting excellent chemo- and regioselectivity under mild reaction conditions. The method avoids the need for pre-formed organometallics and phosphorus halides. Mechanistic and DFT studies suggest that photoexcited [4CzIPN]∗ oxidizes diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate (HEH) to generate the [4CzIPN]•–, which then reduces the alkyl bromide to form alkyl radicals that undergo Giese addition to the vinyl phosphonate. At the same time, Ni0 oxidatively adds the aryl bromide followed by enantiodetermining oxidative radical trapping of the phosphonate-based radical by the tetrahedral NiII center followed by reductive elimination. Independent gradient model based on Hirshfeld partition (IGMH) analysis suggests that the orientation of the phosphonate group (PO … π interaction) is expected to play an essential role in controlling the enantioselectivity.
Related Topics
Concepts
Domino
Enantioselective synthesis
Nickel
Alkyl
Catalysis
Photoredox catalysis
Chemistry
Organic chemistry
Combinatorial chemistry
Photocatalysis
Metadata
- Type
- article
- Language
- en
- Landing Page
- https://doi.org/10.1016/j.gresc.2024.04.001
- OA Status
- diamond
- Cited By
- 4
- References
- 94
- Related Works
- 10
- OpenAlex ID
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All OpenAlex metadata
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https://openalex.org/W4394619980Canonical identifier for this work in OpenAlex
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https://doi.org/10.1016/j.gresc.2024.04.001Digital Object Identifier
- Title
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Enantioselective domino alkyl arylation of vinyl phosphonates by combining photoredox and nickel catalysisWork title
- Type
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articleOpenAlex work type
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enPrimary language
- Publication year
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2024Year of publication
- Publication date
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2024-04-09Full publication date if available
- Authors
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Tingzhi Lin, Guorong Li, Qianqian Lü, Chen Zhang, Yan‐En Wang, Fei Xing, Yundong Xu, Kun Yang, Dan Xiong, Xiufang Xu, Patrick J. Walsh, Jianyou MaoList of authors in order
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https://doi.org/10.1016/j.gresc.2024.04.001Publisher landing page
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YesWhether a free full text is available
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diamondOpen access status per OpenAlex
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https://doi.org/10.1016/j.gresc.2024.04.001Direct OA link when available
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Domino, Enantioselective synthesis, Nickel, Alkyl, Catalysis, Photoredox catalysis, Chemistry, Organic chemistry, Combinatorial chemistry, PhotocatalysisTop concepts (fields/topics) attached by OpenAlex
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4Total citation count in OpenAlex
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2025: 2, 2024: 2Per-year citation counts (last 5 years)
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94Number of works referenced by this work
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10Other works algorithmically related by OpenAlex
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