Details

Autor(en) / Beteiligte

• García-Fernández, Pedro D
• Izquierdo, Cristina
• Iglesias-Sigüenza, Javier
• Díez, Elena
• Fernández, Rosario
• Lassaletta, José M

Titel

Au I -Catalyzed Haloalkynylation of Alkenes

Ist Teil von

• Chemistry : a European journal, 2020-01, Vol.26 (3), p.629-633

Ort / Verlag

Germany

Erscheinungsjahr

2020

Quelle

Wiley Blackwell Single Titles

Beschreibungen/Notizen

• 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.