Although most mechanistic studies on gold-catalysed reactions focused on alkynes as substrates, some knowledge about gold-catalysed conversions of allenic substrates has been obtained. This contribution summarises these insights into the reaction mechanisms of gold-catalysed transformations of allenes which are based on computational studies, labelling studies, the detection of intermediates, chirality transfer and diastereoselective product formation.
From terminal alkynes to glyoxals: Terminal alkynes can be oxidized under mild conditions by the use of an N-oxide in the presence of a gold catalyst. The intermediate glyoxal derivatives can be transferred in a one-pot procedure to substituted quinoxalines (see scheme).
A fast protocol has been developed for the construction of 2-aryl-substituted pyridine derivatives by the oxygen-promoted, ligand-free, Pd(OAc)2-catalyzed Suzuki reaction of 2-halogenated pyridines in aqueous isopropanol.
New perspectives, in particular for the synthesis of isochromane derivatives (see scheme), are provided by the title reaction. Excellent diastereoselectivites are achieved in this reaction which proceeds through a gold‐catalyzed 1,3‐acyloxy migration. In some cases exclusively the Z isomer is detected.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.