Synlett 2014; 25(09): 1241-1245
DOI: 10.1055/s-0033-1341200
letter
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Carbonylation of Aryl Bromides with N-Substituted Cyanamides

Zhong Lian
a   Center for Insoluble Protein Structures, Interdisciplinary Nanoscience Center, Department of Chemistry, Aarhus University, Gustav Wieds Vej 14, 8000 Aarhus C, Denmark
,
Stig D. Friis
a   Center for Insoluble Protein Structures, Interdisciplinary Nanoscience Center, Department of Chemistry, Aarhus University, Gustav Wieds Vej 14, 8000 Aarhus C, Denmark
,
Anders T. Lindhardt*
b   Department of Engineering, Aarhus University, Finlandsgade 22, 8200 Aarhus N, Denmark   Fax: +4541893001   Email: lindhardt@eng.au.dk   Email: ts@chem.au.dk
,
Troels Skrydstrup*
a   Center for Insoluble Protein Structures, Interdisciplinary Nanoscience Center, Department of Chemistry, Aarhus University, Gustav Wieds Vej 14, 8000 Aarhus C, Denmark
› Author Affiliations
Further Information

Publication History

Received: 20 February 2014

Accepted after revision: 19 March 2014

Publication Date:
11 April 2014 (online)


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Abstract

The palladium(0)-catalyzed three-component coupling reaction of aryl bromides, carbon monoxide, and N-alkyl cyan­amides has been developed employing a two-chamber system with ex situ generation of carbon monoxide from a silacarboxylic acid. The reactions proceeded well and were complete with a reaction time of only five hours leading to the corresponding N-alkyl cyanamides in good yields. The methodology was further extended to 13C isotope labeling of the carbonyl group through the use of a 13CO produced from the corresponding 13C-labeled version of the sila­carboxylic acid.

Supporting Information