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

被引：13
作者：
Vaith, Jakub [1 ]
Rodina, Dasha [1 ]
Spaulding, Gregory C. [1 ]
Paradine, Shauna M. [1 ]
机构：
[1] Univ Rochester, Dept Chem, Rochester, NY 14627 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2022年 / 144卷 / 15期
关键词：
SUZUKI COUPLING REACTIONS; HETEROCYCLIC CARBENES; HECK ARYLATION; ARYL; METAL; COMPLEXES; CARBOANNULATION; DERIVATIVES; SELECTIVITY; CYCLIZATION;
D O I：
10.1021/jacs.2c01019
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
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.
引用
收藏
页码：6667 / 6673
页数：7
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