Au I -Catalyzed Haloalkynylation of Alkenes

The formal insertion of alkenes into aromatic chloro- and bromoalkynes takes place under cationic gold catalysis. This haloalkynylation reaction can be performed with cyclic, gem-disubstituted and monosubstituted alkenes, using BINAP, triazolo[4,3-b]isoquinolin-3-ylidene ligands or SPhos, respective...

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Bibliographic Details
Published in:Chemistry : a European journal 2020-01, Vol.26 (3), p.629-633
Main Authors: García-Fernández, Pedro D, Izquierdo, Cristina, Iglesias-Sigüenza, Javier, Díez, Elena, Fernández, Rosario, Lassaletta, José M
Format: Article
Language:English
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Summary:The formal insertion of alkenes into aromatic chloro- and bromoalkynes takes place under cationic gold catalysis. This haloalkynylation reaction can be performed with cyclic, gem-disubstituted and monosubstituted alkenes, using BINAP, triazolo[4,3-b]isoquinolin-3-ylidene ligands or SPhos, respectively. The products were isolated in moderate to excellent yields and with complete diastereo- and regioselectivity; the halogen atom bonding the more substituted carbon of the alkene. Preliminary experiments showed that the enantioselective haloalkynylation of cyclopentene can be performed with (S)-BINAP to afford the insertion products with moderate to good enantioselectivities.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201905078