Directed C–H Functionalization of the Adamantane Framework

Abstract

This review summarizes the synthetic approaches towards 1,2-substitution pattern on the adamantane framework. Selected are the works containing the directed C–H functionalization step.1 Introduction2 Access to 1,2-Disubstituted Derivatives via C–H Insertion Reactions of Electrophilic Organic Species3 Access to 1,2-Disubstituted Derivatives through Hydrogen Radical Abstraction Reactions4 Access to 1,2-Disubstituted Derivatives Exploiting Metal-Catalyzed (Promoted) C–H Activations5 Access to 1,2-Disubstituted Derivatives via Hydride Shift6 Conclusion7 Acronyms

An asymmetric Salamo-based Zn complex supported on Fe3O4 MNPs: a novel heterogeneous nanocatalyst for the silyl protection and deprotection of alcohols under mild conditions

“…Besides, R 3 SiCl, MeSiN ¼ C(Me)OSiMe, Me 3 SiCl, or Me 3 SiOTf in the presence of base are the reagents applied in the traditional and conventional processes. 12,[21][22][23][24][25][26][27][28][29] Moreover, hexamethyldisilazane (HMDS) is a stable, commercially available and inexpensive reagent that can be used for the protection of hydroxy bearing compounds to trimethylsilyl ethers. [30][31][32] Its handling does not require special precautions, and the workup is not timeconsuming because the by-product of the reaction is ammonia, which is easily removed from the reaction medium.…”

Photocatalytic Radical Addition to Levoglucosenone

“…The reaction with adamantane gave two products 9 c and 9 d . Adamantane derivatives are of high interest in many domains such as medicinal chemistry [26,27] . The first product resulted from hydrogen abstraction at the carbon atom in position 1 while 9 d was formed through C‐H bond cleavage at the CH 2 moiety (position 2) of the adamantane.…”

Lipophilic Guanylhydrazone Analogues as Promising Trypanocidal Agents: An Extended SAR Study

“…The synthesis of 1,2-disubstituted adamantane derivatives was the key step for the preparation of analogues described in this study and was achieved by rearrangement of the protoadamantane framework [150]. The starting compound, protoadamantanone 13, was synthesized by Majerski's group for the first time in 1979.…”