Synthesis of rigid tetrahedral tetrafunctional molecules from 1,3,5,7-tetrakis(4-iodophenyl)adamantane

Abstract

1,3,5,7-Tetrakis(4-iodophenyl)adamantane was prepared from 1-bromoadamantane in overall yields of ca. 50%. Conversion to several derivatives occurred in good yields: palladium-catalyzed coupling with 2-methyl-3-butyn-2-ol followed by deprotection gave the tetrakis(phenylacetylide), and reaction with phenyl boronic acid gave the tetrakis(biphenyl)adamantane with all-para linkages. The tetrakis(4-iodophenyl) adamantane offers broad potential for synthesis of star, dendritic, and hyperbranched structures with enforced tetrahedral symmetry derived from the rigid adamantane core.