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

AI McKay; WAO Altalhi; LE McInnes; ML Czyz; AJ Canty; PS Donnelly; RAJ O'Hair

Journal article

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

AI McKay, WAO Altalhi, LE McInnes, ML Czyz, AJ Canty, PS Donnelly, RAJ O'Hair

Journal of Organic Chemistry | AMER CHEMICAL SOC | Published : 2020

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.

University of Melbourne Researchers

Milena Czyz Author

Paul Donnelly Author

Richard O'Hair Author

Related Projects (1)

Metal-promoted bond functionalisation: New routes to amides and thioamides

This project aims to discover new metal-promoted methods to synthesise amides and thioamides, important structural motifs in chemistry and b..

Grants

Awarded by Prince Sattam bin Abdulaziz University

Funding Acknowledgements

We thank the Australian Research Council for financial support (DP180101187 to R.A.J.O., P.S.D., and AJ.C.). We thank Dr. Anastasios Polyzos for useful discussions. W.A. thanks Prince Sattam Bin Abdulaziz University for the award of a scholarship, while M.L.C. acknowledges the ARC for the award of an ITTC Postdoctoral Fellowship.