Skeletal Reconstruction of 3‑Alkylidenepyrrolidines to Azepines Enabled by Pd-Catalyzed C–N Bond Cleavage

Herein we report a Pd-catalyzed C–N bond cleavage strategy for the cycloaddition of pyrrolidines with azlactones or butenolides to construct the azepines. Leverage of the readily accessible 3-alkylidenepyrrolidine can serve as an effective precursor for zwitterionic salts. The in situ formation of a...

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Bibliographic Details
Published in:ACS catalysis 2021-02, Vol.11 (3), p.1774-1779
Main Authors: Wu, Licheng, Wang, Tong, Gao, Chenyang, Huang, Wenyi, Qu, Jingping, Chen, Yifeng
Format: Article
Language:English
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Summary:Herein we report a Pd-catalyzed C–N bond cleavage strategy for the cycloaddition of pyrrolidines with azlactones or butenolides to construct the azepines. Leverage of the readily accessible 3-alkylidenepyrrolidine can serve as an effective precursor for zwitterionic salts. The in situ formation of an allyl-palladium intermediate through the cleavage of inert, cyclic C–N bonds leads to a cascade [5 + 2] cycloaddition, which allows for the diverse synthesis of azepine scaffolds with good functional group tolerance and 100% atom economy.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.1c00130