Towards 3-(2-adamantylidene)diamantane derivatives through the McMurry cross coupling reaction

Abstract

Diamondoid assemblies have a potential in nanoelectronics as the substrates for self-assembled monolayer formation. However, selective functionalization of such molecules is cumbersome. We demonstrate that the McMurry cross-coupling reaction is useful for the preparation of 3-(2-adamantylidene)diamantane derivatives with substituents at the tertiary and secondary positions of the diamantane moiety. This allows to create the surface attachment points in the diamondoid structure.

Recent advances of carbonyl olefination via McMurry coupling reaction

“…In 2018, A novel synthetic of diamondoids compound, especially adamantane, 190, has also been reached by Hoc et al using the McMurry reaction. 104 Diamondoid is an unusual molecule that has been widely applied in geochemistry since 1990 due to its peculiar cage molecular structure. Both diamondoid and its derivatives are contained naturally in oil and fossil deposits with a 1–100 ppm concentration.…”

“…Both diamondoid and its derivatives are contained naturally in oil and fossil deposits with a 1–100 ppm concentration. 104 The low series of diamondoids plays a vital role in designing and synthesizing drug delivery systems. The experimental results showed that the McMurry coupling of diamantanone and amantanone was successful with high product yields.…”