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Updated: Sep 28, 2025

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
Pd-Catalyzed Heteroannulation Using N-Arylureas as a Sterically Undemanding Ligand Platform
Jakub Vaith1, Dasha Rodina1, Gregory C Spaulding1
1Department of Chemistry, University of Rochester, Rochester, New York 14627, United States.
Abstract:
We report the development of ureas as sterically undemanding pro-ligands for Pd catalysis. N-Arylureas outperform phosphine ligands for the Pd-catalyzed heteroannulation of N-tosyl-o-bromoanilines and 1,3-dienes, engaging diverse coupling partners for the preparation of 2-subsituted indolines, including sterically demanding substrates that have not previously been tolerated. Experimental and computational studies on model Pd-urea and Pd-ureate complexes are consistent with monodentate binding through the nonsubstituted nitrogen, which is uncommon for metal-ureate complexes.
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