Priebbenow Daniel L, Hua Carol
School of Chemistry, The University of Melbourne, Parkville, Victoria, 3010, Australia.
Chem Commun (Camb). 2021 Aug 10;57(64):7938-7941. doi: 10.1039/d1cc03051e.
Studies into the Cp*Rh(iii)-catalysed hydroarylation of alkenes with aryl acyl silanes led to the discovery of a new synthetic strategy to access unique silicon derived indene frameworks. Rather than protodemetalation of the metal enolate formed following insertion of an alkene into the aryl C-H bond, intramolecular aldol condensation of the acyl silane occurred to generate a series of 2-formyl- and 2-acetyl-3-silyl indenes. This represents only the second example of rhodium-catalysed C-H functionalisation employing acyl silanes as weakly coordinating directing groups and the intramolecular aldol condensation strategy was extended to access analogous silicon derived benzofurans.
