Identification of the Side Products That Diminish the Yields of the Monoamidated Product in Metal-Catalyzed C-H Amidation of 2-Phenylpyridine with Arylisocyanates

Alasdair I McKay; Weam A O Altalhi; Lachlan E McInnes; Milena L Czyz; Allan J Canty; Paul S Donnelly; Richard A J O'Hair

doi:10.1021/acs.joc.9b02831

Identification of the Side Products That Diminish the Yields of the Monoamidated Product in Metal-Catalyzed C-H Amidation of 2-Phenylpyridine with Arylisocyanates

J Org Chem. 2020 Feb 21;85(4):2680-2687. doi: 10.1021/acs.joc.9b02831. Epub 2020 Jan 23.

Authors

Alasdair I McKay^{1

2}, Weam A O Altalhi^{1

2}, Lachlan E McInnes^{1

2}, Milena L Czyz¹, Allan J Canty³, Paul S Donnelly^{1

2}, Richard A J O'Hair^{1

2}

Affiliations

¹ School of Chemistry , The University of Melbourne , Melbourne , Victoria 3010 , Australia.
² Bio21 Institute of Molecular Science and Biotechnology , The University of Melbourne , Melbourne , Victoria 3010 , Australia.
³ School of Natural Sciences-Chemistry , University of Tasmania , Private Bag 75 , Hobart , Tasmania 7001 , Australia.

PMID: 31971390
DOI: 10.1021/acs.joc.9b02831

Abstract

The Ru(II)-catalyzed amidation of 2-arylpyridines with aryl isocyanates via C-H bond activation is less efficient than described previously, due to the formation of a series of side products, which were readily identified using direct infusion electrospray mass spectrometry and high-performance liquid chromatography-mass spectrometry.

Publication types

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