Palladium-catalyzed double carbonylation using near stoichiometric carbon monoxide: expedient access to substituted 13C2-labeled phenethylamines

Dennis U Nielsen; Karoline Neumann; Rolf H Taaning; Anders T Lindhardt; Amalie Modvig; Troels Skrydstrup

doi:10.1021/jo3009337

Palladium-catalyzed double carbonylation using near stoichiometric carbon monoxide: expedient access to substituted 13C2-labeled phenethylamines

J Org Chem. 2012 Jul 20;77(14):6155-65. doi: 10.1021/jo3009337. Epub 2012 Jul 11.

Authors

Dennis U Nielsen¹, Karoline Neumann, Rolf H Taaning, Anders T Lindhardt, Amalie Modvig, Troels Skrydstrup

Affiliation

¹ Department of Chemistry, Center for Insoluble Protein Structures (InSPIN), and the Interdisciplinary Nanoscience Center (iNANO), Aarhus University, Langelandsgade 140, 8000 Aarhus C, Denmark.

PMID: 22725263
DOI: 10.1021/jo3009337

Abstract

A novel and general approach for (13)C(2)- and (2)H-labeled phenethylamine derivatives has been developed, based on a highly convergent single-step assembly of the carbon skeleton. The efficient incorporation of two carbon-13 isotopes into phenethylamines was accomplished using a palladium-catalyzed double carbonylation of aryl iodides with near stoichiometric carbon monoxide.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carbon Isotopes
Carbon Monoxide / chemistry*
Catalysis
Molecular Structure
Organometallic Compounds / chemistry*
Palladium / chemistry*
Phenethylamines / chemical synthesis*
Phenethylamines / chemistry

Substances

Carbon Isotopes
Organometallic Compounds
Phenethylamines
Palladium
Carbon Monoxide