Alkoxydienes via Copper-Promoted Couplings: Utilizing an Alkyne Effect
- 28 April 2010
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 12 (11), 2508-2510
- https://doi.org/10.1021/ol100707s
Abstract
Simple alkenes and alkynes, with 3-hexyne in particular, are found to be important π 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.Keywords
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