Cooperative Iodide Pd(0)-Catalysed Coupling of Alkoxyallenes and N-Tosylhydrazones: A Selective Synthesis of Conjugated and Skipped Dienes

Stefano Parisotto; Lorenzo Palagi; Cristina Prandi; Annamaria Deagostino

doi:10.1002/chem.201800765

Cooperative Iodide Pd(0)-Catalysed Coupling of Alkoxyallenes and N-Tosylhydrazones: A Selective Synthesis of Conjugated and Skipped Dienes

Chemistry. 2018 Apr 11;24(21):5484-5488. doi: 10.1002/chem.201800765. Epub 2018 Mar 23.

Authors

Stefano Parisotto¹, Lorenzo Palagi¹, Cristina Prandi¹, Annamaria Deagostino¹

Affiliation

¹ Department of Chemistry, University of Torino, Via Giuria 7, Torino, 10125, Italy.

PMID: 29493826
DOI: 10.1002/chem.201800765

Abstract

Palladium(0)-catalysed hydro-alkylation or -alkenylation of alkoxyallenes with N-tosylhydrazones gives direct access to conjugated and skipped 1-alkoxydienes with high efficiency and excellent functional-group compatibility. The reaction is proposed to involve the in situ-formed t-butanol as proton source in the key step of the allylpalladium(II) species generation. Moreover, lithium iodide or iodobenzene are employed as an unprecedented iodide (I^- ) reservoir to sustain the catalytic cycle.

Keywords: alkoxyallenes; dienes; iodide; palladium; tosylhydrazones.