Efficient Preparation of Apically Substituted Diamondoid Derivatives

Abstract

We present an effective three-step chromatography-free sequence for the preparation of apical monohydroxy derivatives of diamantane, triamantane, and [121]tetramantane from the corresponding bis-apical diols utilizing tert-butyldimethylsilyl chloride as the monosilylating agent. The procedure was successfully applied to the monoprotection of several other aliphatic and aromatic diols. Additionally, 9-aminodiamantan-4-carboxylic acid, which has significant potential in medicinal and material sciences, was prepared through Ritter reaction of 4,9-dihydroxydiamantane in trifluoroacetic acid.

Photocatalytic dehydrations for the Ritter reaction

“…1 A powerful method for amide synthesis through C–N bond formation is known as the Ritter reaction. 2 In the past decades, various types of substrates have been used for the Ritter reactions. 3 In recent years, photoredox catalysis 4 has emerged and further demonstrated the utility of this long-established amination reaction by avoidance of strong acids, stoichiometric oxidants and/or high temperatures.…”