Gold(I)-catalyzed intermolecular oxyarylation of alkynes: unexpected regiochemistry in the alkylation of arenes.
The reaction between acetylenes and sulfoxides, studied as a test case for gold-catalyzed intermolecular addition, provides the oxyarylation compounds 3 in good yields. Unpredictably, in all cases a single regioisomer arising from the electrophilic aromatic alkylation at the position adjacent to the sulfur atom is obtained instead of the expected Friedel-Crafts regioisomer. A new concerted mechanism based on DFT calculations is proposed to account for the products in this intermolecular gold(I)-catalyzed reaction.
Departamento de Química Orgánica, Universidad de Valencia, 46100 Burjassot, Valencia, Spain.
Ana B
AB
Cuenca
Sergi
S
Montserrat
Kabir M
KM
Hossain
Gisela
G
Mancha
Agustí
A
Lledós
Mercedes
M
Medio-Simón
Gregori
G
Ujaque
Gregorio
G
Asensio