Pd-Catalyzed Heteroannulation Using N-Arylureas as a Sterically Undemanding Ligand Platform

[Image: see text] 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-subsitute...

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Autores principales: Vaith, Jakub, Rodina, Dasha, Spaulding, Gregory C., Paradine, Shauna M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9026275/
https://www.ncbi.nlm.nih.gov/pubmed/35380831
http://dx.doi.org/10.1021/jacs.2c01019
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author Vaith, Jakub
Rodina, Dasha
Spaulding, Gregory C.
Paradine, Shauna M.
author_facet Vaith, Jakub
Rodina, Dasha
Spaulding, Gregory C.
Paradine, Shauna M.
author_sort Vaith, Jakub
collection PubMed
description [Image: see text] 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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spelling pubmed-90262752022-04-25 Pd-Catalyzed Heteroannulation Using N-Arylureas as a Sterically Undemanding Ligand Platform Vaith, Jakub Rodina, Dasha Spaulding, Gregory C. Paradine, Shauna M. J Am Chem Soc [Image: see text] 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. American Chemical Society 2022-04-05 2022-04-20 /pmc/articles/PMC9026275/ /pubmed/35380831 http://dx.doi.org/10.1021/jacs.2c01019 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Vaith, Jakub
Rodina, Dasha
Spaulding, Gregory C.
Paradine, Shauna M.
Pd-Catalyzed Heteroannulation Using N-Arylureas as a Sterically Undemanding Ligand Platform
title Pd-Catalyzed Heteroannulation Using N-Arylureas as a Sterically Undemanding Ligand Platform
title_full Pd-Catalyzed Heteroannulation Using N-Arylureas as a Sterically Undemanding Ligand Platform
title_fullStr Pd-Catalyzed Heteroannulation Using N-Arylureas as a Sterically Undemanding Ligand Platform
title_full_unstemmed Pd-Catalyzed Heteroannulation Using N-Arylureas as a Sterically Undemanding Ligand Platform
title_short Pd-Catalyzed Heteroannulation Using N-Arylureas as a Sterically Undemanding Ligand Platform
title_sort pd-catalyzed heteroannulation using n-arylureas as a sterically undemanding ligand platform
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9026275/
https://www.ncbi.nlm.nih.gov/pubmed/35380831
http://dx.doi.org/10.1021/jacs.2c01019
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