Mechanistic insights into the gold-catalyzed cycloisomerization of bromoallenyl ketones: ligand-controlled regioselectivity.
Through computational and experimental studies, the mechanisms of gold-catalyzed cycloisomerization of bromoallenyl ketones in toluene have been elucidated. The divergent 1,2-migrations for the Au(I)- and Au(III)-catalyzed reactions have been investigated, and the results confirmed that the regiochemistry is ligand-dependent in cases of Au(PR3)L (L = Cl, OTf, BF4, and SbF6) catalysts.
Xia
Yuanzhi
Y
Key Laboratory of Organic Synthesis of Jiangsu Province, Department of Chemistry and Chemical Engineering, Suzhou University, Suzhou 215006, China.
Dudnik
Alexander S
AS
Gevorgyan
Vladimir
V
Li
Yahong
Y
D000466:Alkadienes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis*; D006046:Gold / Q000737:chemistry*; D006842:Hydrocarbons, Brominated / Q000737:chemistry; D007536:Isomerism; D007659:Ketones / Q000737:chemistry*; D011789:Quantum Theory; D013816:Thermodynamics
D000466:Alkadienes; D005663:Furans; D006842:Hydrocarbons, Brominated; D007659:Ketones; C025947:propadiene; D006046:Gold