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AuI-Catalyzed Haloalkynylation of Alkenes

AuthorsGarcía-Fernández, Pedro D.; Izquierdo, Cristina; Iglesias-Sigüenza, Javier; Díez, Elena; Fernández, Rosario; Lassaletta, José M.
Issue Date2020
PublisherJohn Wiley & Sons
CitationChemistry - A European Journal 26: 629- 633 (2020)
AbstractThe 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.
Publisher version (URL)http://dx.doi.org/10.1002/chem.201905078
Identifiersdoi: 10.1002/chem.201905078
issn: 1521-3765
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