Palladium-Catalyzed Oxidative Difunctionalization of Alkenes with α-Carbonyl Alkyl Bromides Initiated through a Heck-type Insertion: A Route to Indolin-2-ones†
Jian-Hong Fan
State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (China)
Search for more papers by this authorWen-Ting Wei
State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (China)
Search for more papers by this authorMing-Bo Zhou
State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (China)
Search for more papers by this authorDr. Ren-Jie Song
State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (China)
Search for more papers by this authorCorresponding Author
Prof. Dr. Jin-Heng Li
State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (China)
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 (China)
State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (China)Search for more papers by this authorJian-Hong Fan
State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (China)
Search for more papers by this authorWen-Ting Wei
State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (China)
Search for more papers by this authorMing-Bo Zhou
State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (China)
Search for more papers by this authorDr. Ren-Jie Song
State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (China)
Search for more papers by this authorCorresponding Author
Prof. Dr. Jin-Heng Li
State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (China)
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 (China)
State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (China)Search for more papers by this authorWe thank the Natural Science Foundation of China (21172060), the Specialized Research Fund for the Doctoral Program of Higher Education (20120161110041), and the Hunan Provincial Natural Science Foundation of China (13JJ2018) for financial support.
Graphical Abstract
Indolinone synthesis: A new palladium-catalyzed oxidative difunctionalization reaction of N-arylalkenes with primary, secondary, and tertiary α-carbonyl alkyl bromides proceeds through a radical process and provides indolin-2-ones in moderate to excellent yields. The reaction is initiated by a Heck insertion followed by interception of the σ-alkyl palladium(II) intermediate with aryl C(sp2)H bonds. dppe=1,2-bis(diphenylphosphino)ethane.
Abstract
The oxidative interception of various σ-alkyl palladium(II) intermediates with additional reagents for the difunctionalization of alkenes is an important research area. A new palladium-catalyzed oxidative difunctionalization reaction of alkenes with α-carbonyl alkyl bromides is described, in which the σ-alkyl palladium(II) intermediate is generated through a Heck insertion and trapped using an aryl C(sp2)H bond. This method can be applied to various α-carbonyl alkyl bromides, including primary, secondary, and tertiary α-bromoalkyl esters, ketones, and amides.
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