Easily Accessible Auxiliary for Palladium-Catalyzed Intramolecular Amination of C(sp2)H and C(sp3)H Bonds at δ- and ε-Positions†
Chao Wang
Key Laboratory of Organic Synthesis of Jiangsu Province College of Chemistry, Chemical Engineering and Materials Science Soochow University, Suzhou 215123 (P.R. China)
Search for more papers by this authorChangpeng Chen
Key Laboratory of Organic Synthesis of Jiangsu Province College of Chemistry, Chemical Engineering and Materials Science Soochow University, Suzhou 215123 (P.R. China)
Search for more papers by this authorJingyu Zhang
Key Laboratory of Organic Synthesis of Jiangsu Province College of Chemistry, Chemical Engineering and Materials Science Soochow University, Suzhou 215123 (P.R. China)
Search for more papers by this authorJian Han
Key Laboratory of Organic Synthesis of Jiangsu Province College of Chemistry, Chemical Engineering and Materials Science Soochow University, Suzhou 215123 (P.R. China)
Search for more papers by this authorQian Wang
Key Laboratory of Organic Synthesis of Jiangsu Province College of Chemistry, Chemical Engineering and Materials Science Soochow University, Suzhou 215123 (P.R. China)
Search for more papers by this authorKun Guo
Key Laboratory of Organic Synthesis of Jiangsu Province College of Chemistry, Chemical Engineering and Materials Science Soochow University, Suzhou 215123 (P.R. China)
Search for more papers by this authorPei Liu
Key Laboratory of Organic Synthesis of Jiangsu Province College of Chemistry, Chemical Engineering and Materials Science Soochow University, Suzhou 215123 (P.R. China)
Search for more papers by this authorMingyu Guan
Key Laboratory of Organic Synthesis of Jiangsu Province College of Chemistry, Chemical Engineering and Materials Science Soochow University, Suzhou 215123 (P.R. China)
Search for more papers by this authorCorresponding Author
Dr. Yingming Yao
Key Laboratory of Organic Synthesis of Jiangsu Province College of Chemistry, Chemical Engineering and Materials Science Soochow University, Suzhou 215123 (P.R. China)
Key Laboratory of Organic Synthesis of Jiangsu Province College of Chemistry, Chemical Engineering and Materials Science Soochow University, Suzhou 215123 (P.R. China)Search for more papers by this authorCorresponding Author
Prof. Dr. Yingsheng Zhao
Key Laboratory of Organic Synthesis of Jiangsu Province College of Chemistry, Chemical Engineering and Materials Science Soochow University, Suzhou 215123 (P.R. China)
Key Laboratory of Organic Synthesis of Jiangsu Province College of Chemistry, Chemical Engineering and Materials Science Soochow University, Suzhou 215123 (P.R. China)Search for more papers by this authorChao Wang
Key Laboratory of Organic Synthesis of Jiangsu Province College of Chemistry, Chemical Engineering and Materials Science Soochow University, Suzhou 215123 (P.R. China)
Search for more papers by this authorChangpeng Chen
Key Laboratory of Organic Synthesis of Jiangsu Province College of Chemistry, Chemical Engineering and Materials Science Soochow University, Suzhou 215123 (P.R. China)
Search for more papers by this authorJingyu Zhang
Key Laboratory of Organic Synthesis of Jiangsu Province College of Chemistry, Chemical Engineering and Materials Science Soochow University, Suzhou 215123 (P.R. China)
Search for more papers by this authorJian Han
Key Laboratory of Organic Synthesis of Jiangsu Province College of Chemistry, Chemical Engineering and Materials Science Soochow University, Suzhou 215123 (P.R. China)
Search for more papers by this authorQian Wang
Key Laboratory of Organic Synthesis of Jiangsu Province College of Chemistry, Chemical Engineering and Materials Science Soochow University, Suzhou 215123 (P.R. China)
Search for more papers by this authorKun Guo
Key Laboratory of Organic Synthesis of Jiangsu Province College of Chemistry, Chemical Engineering and Materials Science Soochow University, Suzhou 215123 (P.R. China)
Search for more papers by this authorPei Liu
Key Laboratory of Organic Synthesis of Jiangsu Province College of Chemistry, Chemical Engineering and Materials Science Soochow University, Suzhou 215123 (P.R. China)
Search for more papers by this authorMingyu Guan
Key Laboratory of Organic Synthesis of Jiangsu Province College of Chemistry, Chemical Engineering and Materials Science Soochow University, Suzhou 215123 (P.R. China)
Search for more papers by this authorCorresponding Author
Dr. Yingming Yao
Key Laboratory of Organic Synthesis of Jiangsu Province College of Chemistry, Chemical Engineering and Materials Science Soochow University, Suzhou 215123 (P.R. China)
Key Laboratory of Organic Synthesis of Jiangsu Province College of Chemistry, Chemical Engineering and Materials Science Soochow University, Suzhou 215123 (P.R. China)Search for more papers by this authorCorresponding Author
Prof. Dr. Yingsheng Zhao
Key Laboratory of Organic Synthesis of Jiangsu Province College of Chemistry, Chemical Engineering and Materials Science Soochow University, Suzhou 215123 (P.R. China)
Key Laboratory of Organic Synthesis of Jiangsu Province College of Chemistry, Chemical Engineering and Materials Science Soochow University, Suzhou 215123 (P.R. China)Search for more papers by this authorWe are grateful to Dr. Aiwen Lei (Wuhan University) for helpful suggestions and comments on this manuscript. We gratefully acknowledge financial support from the Natural Science Foundation of Jiangsu Province of China (L210903913), and a start-up fund (Q410901212) from Soochow University for support of this work. The PAPD and Qing Lan Project are also gratefully acknowledged.
Graphical Abstract
Remote access: The first application of an oxalyl amide to direct CH functionalizations at remote positions is reported. The results show both C(sp2)H and C(sp3)H bonds at δ- and ε-positions are effectively activated, thus giving tetrahydroquinolines, benzomorpholines, pyrrolidines, and indolines in moderate to excellent yields by palladium-catalyzed intramolecular CH amination.
Abstract
An easily synthesized and accessible N,O-bidentate auxiliary has been developed for selective CH activation under palladium catalysis. The novel auxiliary showed its first powerful application in CH functionalization of remote positions. Both C(sp2)H and C(sp3)H bonds at δ- and ε-positions were effectively activated, thus giving tetrahydroquinolines, benzomorpholines, pyrrolidines, and indolines in moderate to excellent yields by palladium-catalyzed intramolecular CH amination.
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