Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, Indiana 47405-7102, USA.
J Am Chem Soc. 2012 Sep 19;134(37):15297-300. doi: 10.1021/ja307761f. Epub 2012 Sep 7.
A palladium-catalyzed alkyne insertion/Suzuki reaction with unactivated alkyl iodides is described. Under the reaction conditions, selective migratory insertion of alkynes avoids β-hydride elimination and provides a facile synthesis of stereodefined, tetrasubstituted olefins. The transformation offers broad substrate scope for both the alkyl iodide and boron nucleophile. Mechanistic studies have revealed inversion of the stereocenter for the carbon bearing the iodide.
本文描述了钯催化的炔烃插入/Suzuki 反应与未活化的烷基碘化物。在反应条件下，炔烃的选择性迁移插入避免了β-氢消除，为立体定义的四取代烯烃的简便合成提供了可能。该转化对烷基碘化物和硼亲核试剂都具有广泛的底物范围。机理研究表明，带有碘原子的碳原子的立体中心发生了反转。
