Synthesis of\nAxially Chiral Monofluoroalkenes via\nNickel-Catalyzed Reductive Cross-Coupling of <i>gem</i>-Difluoroalkenes

Enantioenriched monofluoroalkenes are important structural\nmotifs\nin life science and functional materials. To date, only limited strategies\nwere reported for the synthesis of monofluoroalkenes with stereogenic\ncarbon centers; the axially chiral counterpart is still highly desirable.\nHerein, we report Ni-catalyzed defluorinative cross-electrophile coupling\nof <i>gem</i>-difluoroalkenes with biaryl electrophiles\nfor the synthesis of axially chiral monofluoroalkenes. The resulting\naxially chiral monofluoroalkenes are formed with excellent regio-\nand stereoselectivities. Synthetic transformation of these axially\nenantioenriched monofluoroalkenes was also demonstrated.

Publication Details

Journal
Figshare
Published
2024-09-13
DOI
https://doi.org/10.1021/acs.orglett.4c03119.s001
Primary Topic
Axial and Atropisomeric Chirality Synthesis
Type
article
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article

Synthesis of\nAxially Chiral Monofluoroalkenes via\nNickel-Catalyzed Reductive Cross-Coupling of gem-Difluoroalkenes

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Axial and Atropisomeric Chirality Synthesis
article

Synthesis of\nAxially Chiral Monofluoroalkenes via\nNickel-Catalyzed Reductive Cross-Coupling of gem-Difluoroalkenes

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Abstract

Enantioenriched monofluoroalkenes are important structural\nmotifs\nin life science and functional materials. To date, only limited strategies\nwere reported for the synthesis of monofluoroalkenes with stereogenic\ncarbon centers; the axially chiral counterpart is still highly desirable.\nHerein, we report Ni-catalyzed defluorinative cross-electrophile coupling\nof <i>gem</i>-difluoroalkenes with biaryl electrophiles\nfor the synthesis of axially chiral monofluoroalkenes. The resulting\naxially chiral monofluoroalkenes are formed with excellent regio-\nand stereoselectivities. Synthetic transformation of these axially\nenantioenriched monofluoroalkenes was also demonstrated.

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Axial and Atropisomeric Chirality Synthesis
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Synthesis of\nAxially Chiral Monofluoroalkenes via\nNickel-Catalyzed Reductive Cross-Coupling of <i>gem</i>-Difluoroalkenes · Figshare (2024) | TGRS Research Map | TGRS