(Hetero)Adamantane Synthesis: A Triple Alkylation Reaction

Abstract (Hetero)adamantanes containing tetrel bridgeheads (C, Si, and Ge) are useful structures in select areas of surface and materials science. The synthesis of diverse (hetero)adamantane-based molecules with interchangeable functional groups for broad applications is an area ripe for innovation. The discovery of an expedient and convergent method for the synthesis of (heteroadamantane) scaffolds is described. The convenient synthetic route proceeding via a triple alkylation reaction represents a breakthrough in accessing the adamantane molecular class. Application of this transformation to the synthesis of (hetero)adamantane-based tripods containing tetrel bridgeheads (C- and Ge-) was explored.