Simple alkenes and alkynes, with 3-hexyne in particular, are found to be important pi ligands for oxidative copper-based coupling (modern Ullmann) reactions. This enabled syntheses of various alkoxydienes with removable protecting groups that are valuable substrates for Diels-Alder reactions from alcohols and vinyl boronate esters. In addition to demonstrating that 3-hexyne is a ligand for copper in both stoichiometric and catalytic reactions, the reaction atmosphere was found to play a critical role.
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Winternheimer et al. (2010) studied this question.
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