7-Aryl-1,3,5-cycloheptatrienes react intermolecularly with methylenecyclopropanes in a triple gold(I)-catalyzed reaction to form cyclopentenes. The same formal (4+1) cycloaddition occurs with cyclobutenes. Other precursors of gold(I) carbenes can also be used as the C1 component of the cycloaddition.
The potential of mercury catalysis has been extended to the arena of enolate umpolung reactions for the first time by the generation of enolonium species via Hg(OTf) 2 -catalyzed N-oxide addition to alkynes. The enolonium species formed can undergo intramolecular nucleophilic attack by hydroxyl or amino groups, leading to the synthesis of various coumaran-3-ones and indolin-3-ones.
The polycyclisation of polyenynes catalyzed by gold(i) has been extended for the first time to the simultaneous formation of up to four carbon-carbon bonds, leading to steroid-like molecules with high stereoselectivity in a single step with low catalyst loadings. In addition to terminal alkynes, bromoalkynes can also be used as initiators of polyene cyclisations, giving rise to synthetically useful cyclic bromoalkenes.
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.