OXIDATIVE DIMERIZATION REACTIONS AND REACTIVITY OF TERMINAL ACETYLENIC ALCOHOLS
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This review article provides a systematic analysis of literature data on the oxidative dimerization reactions and reactivity of terminal acetylenic alcohols. Particular attention is paid to the reactivity of the terminal C(sp)–H bond, the chemical principles underlying the formation of conjugated diynediols, and the key stages of the oxidative coupling process. Catalytic systems, oxidants, ligands, bases, and solvents employed in oxidative dimerization are summarized with emphasis on their effects on reaction efficiency and selectivity. The influence of the molecular structure of terminal acetylenic alcohols, including the electronic and steric effects of the hydroxyl group and substituents, on their dimerization behavior is also discussed. Based on published studies, classical and modern catalytic approaches to the synthesis of hydroxyl-containing conjugated diynes are compared, and the prospects for further development of this transformation in organic synthesis are outlined.
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References
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