Synthesis 2003(18): 2886-2889  
DOI: 10.1055/s-2003-42478
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart · New York

Palladium-Imidazolium N-Heterocyclic Carbene-Catalyzed Carbonylative Amidation With Boronic Acids, Aryl Diazonium Ions, and Ammonia

Yudao Maa, Chun Songb, Qiang Chaic, Changqin Maa, Merritt B. Andrus*b
a Chemistry College of Shandong University, Shanda Road #100, Jinan, Shandong 250100, P. R. China
b Department of Chemistry and Biochemistry, Brigham Young University, C100 BNSN, Provo, Utah 84602, USA
Fax: +(801)4220153; e-Mail: mbandrus@chem.byu.edu;
c Shandong Academy of Medical Science, Jinan, Shandong 250062, P. R. China
Further Information

Publication History

Received 8 October 2003
Publication Date:
12 November 2003 (online)

Abstract

Aryl diazonium tetrafluoroborates have been coupled with arylboron compounds, carbon monoxide, and ammonia to give aryl amides in high yields. A saturated N-heterocyclic carbene (NHC) ligand, H2IPr was used with palladium(II) acetate to give the active catalyst. A mechanism is proposed for this novel four-component coupling reaction.