CuF2/DMAP-Catalyzed N‑Vinylation: Scope and Mechanistic Study

CuF2/DMAP has been established as an excellent catalytic system for vinylsilane-promoted N-vinylation of amides and azoles at room temperature without an external fluoride source. A mechanism has been proposed on the basis of the isolation of reactive intermediate [Cu­(DMAP)4Cl2], fluoride ion-assis...

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Bibliographic Details
Published in:Organic letters 2023-03, Vol.25 (8), p.1235-1240
Main Authors: Mondal, Krishanu, Patra, Susanta, Halder, Pallabi, Mukhopadhyay, Narottam, Das, Parthasarathi
Format: Article
Language:English
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Summary:CuF2/DMAP has been established as an excellent catalytic system for vinylsilane-promoted N-vinylation of amides and azoles at room temperature without an external fluoride source. A mechanism has been proposed on the basis of the isolation of reactive intermediate [Cu­(DMAP)4Cl2], fluoride ion-assisted transmetalation, and ultraviolet–visible spectroscopic studies. The catalytic efficiency of the synthesized and structurally characterized [Cu­(DMAP)4Cl2] complex has been demonstrated. The valuable monomers for water-soluble polymers, viz., NVP, NVC, and NVIBA, were synthesized on a gram scale.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c03856