Ruthenium(II) porphyrin-catalyzed amidation of aromatic heterocycles

Ling He; Philip Wai Hong Chan; Wai-Man Tsui; Wing-Yiu Yu; Chi-Ming Che

doi:10.1021/ol049232j

Ruthenium(II) porphyrin-catalyzed amidation of aromatic heterocycles

Org Lett. 2004 Jul 8;6(14):2405-8. doi: 10.1021/ol049232j.

Authors

Ling He¹, Philip Wai Hong Chan, Wai-Man Tsui, Wing-Yiu Yu, Chi-Ming Che

Affiliation

¹ Department of Chemistry and Open Laboratory of Chemical Biology of the Institute of Molecular Technology for Drug Discovery and Synthesis, The University of Hong Kong, Pokfulam Road, Hong Kong, P. R. China.

PMID: 15228290
DOI: 10.1021/ol049232j

Abstract

[reaction: see text] Ruthenium(II) porphyrin-catalyzed amidation of aromatic heterocycles with iminoiodanes under mild conditions (CH(2)Cl(2), 4 A molecular sieves, ultrasound, 40 degrees C) was achieved in moderate to good yields (up to 84%) and conversions (up to 99%). Only the N,N-ditosylamidated product was obtained for reactions involving heteroarenes, where X = O, S, or NTs. N-Alkyl- and N-aryl-substituted pyrroles, on the other hand, were shown to give the 3,4-diaminated adduct.