Rhodium(III)-Catalyzed [3+2] Annulation of 5-Aryl-2,3-dihydro-1H-pyrroles with Internal Alkynes through C(sp2)H/Alkene Functionalization†
Ming-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 authorRui Pi
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 Hu
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 authorYuan Yang
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 authorRen-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
Dr. Yuanzhi Xia
College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035 (China)
Yuanzhi Xia, College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035 (China)
Jin-Heng Li, 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)
Yuanzhi Xia, College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035 (China)
Jin-Heng Li, 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 authorRui Pi
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 Hu
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 authorYuan Yang
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 authorRen-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
Dr. Yuanzhi Xia
College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035 (China)
Yuanzhi Xia, College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035 (China)
Jin-Heng Li, 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)
Yuanzhi Xia, College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035 (China)
Jin-Heng Li, 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 NSFC (No. 21172060) and HPNSFC (No. 13JJ2018) for financial support.
Abstract
This study describes a new rhodium(III)-catalyzed [3+2] annulation of 5-aryl-2,3-dihydro-1H-pyrroles with internal alkynes using a Cu(OAc)2 oxidant for building a spirocyclic ring system, which includes the functionalization of an aryl C(sp2)H bond and addition/protonolysis of an alkene CC bond. This method is applicable to a wide range of 5-aryl-2,3-dihydro-1H-pyrroles and internal alkynes, and results in the assembly of the spiro[indene-1,2′-pyrrolidine] architectures in good yields with excellent regioselectivities.
Supporting Information
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