Premium
CO Extrusion in Homogeneous Gold Catalysis: Reactivity of Gold Acyl Species Generated through Water Addition to Gold Vinylidenes
Author(s) -
Bucher Janina,
Stößer Tim,
Rudolph Matthias,
Rominger Frank,
Hashmi A. Stephen K.
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201409859
Subject(s) - reactivity (psychology) , catalysis , indene , chemistry , homogeneous , steric effects , extrusion , colloidal gold , homogeneous catalysis , combinatorial chemistry , nanotechnology , organic chemistry , materials science , nanoparticle , medicine , physics , alternative medicine , pathology , metallurgy , thermodynamics
Abstract Herein, we describe a new gold‐catalyzed decarbonylative indene synthesis. Synergistic σ,π‐activation of diyne substrates leads to gold vinylidene intermediates, which upon addition of water are transformed into gold acyl species, a type of organogold compound hitherto only scarcely reported. The latter are shown to undergo extrusion of CO, an elementary step completely unknown for homogeneous gold catalysis. By tuning the electronic and steric properties of the starting diyne systems, this new reactivity could be exploited for the synthesis of indene derivatives in high yields.