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Au I ‐Catalyzed Haloalkynylation of Alkenes
Author(s) -
GarcíaFernández Pedro D.,
Izquierdo Cristina,
IglesiasSigüenza Javier,
Díez Elena,
Fernández Rosario,
Lassaletta José M.
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201905078
Subject(s) - enantioselective synthesis , alkene , chemistry , cationic polymerization , regioselectivity , catalysis , cyclopentene , medicinal chemistry , halogen , carbon atom , organic chemistry , ring (chemistry) , alkyl
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.