Palladium-Catalyzed Regiodivergent Substitution of Propargylic Carbonates

Theresa M Locascio; Jon A Tunge

doi:10.1002/chem.201603481

Palladium-Catalyzed Regiodivergent Substitution of Propargylic Carbonates

Chemistry. 2016 Dec 12;22(50):18140-18146. doi: 10.1002/chem.201603481. Epub 2016 Oct 31.

Authors

Theresa M Locascio¹, Jon A Tunge¹

Affiliation

¹ Department of Chemistry, The University of Kansas, 2010 Malott Hall, 1251 Wescoe Hall Drive, Lawrence, KS, 66045, USA.

PMID: 27797416
DOI: 10.1002/chem.201603481

Abstract

The palladium(0)-catalyzed, ligand-controlled, regioselective addition of diaryl acetonitrile pronucleophiles to propargylic carbonates is reported. Selective formation of either terminal 1,3-dienyl or propargylated products is proposed to arise from a change in reaction mechanism controlled by the denticity of the coordinating ligand.

Keywords: coupling; dienylation; palladium; propargylation.