Palladium-Catalyzed anti-Markovnikov Halosulfonamidation of Unactivated Alkene†
Bowen Wang
State Key Laboratory of Pulp and Paper Engineering, Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, Guangdong, 510641 China
Search for more papers by this authorJianxiao Li
State Key Laboratory of Pulp and Paper Engineering, Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, Guangdong, 510641 China
Search for more papers by this authorWanqing Wu
State Key Laboratory of Pulp and Paper Engineering, Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, Guangdong, 510641 China
Search for more papers by this authorCorresponding Author
Huanfeng Jiang
State Key Laboratory of Pulp and Paper Engineering, Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, Guangdong, 510641 China
E-mail: [email protected]Search for more papers by this authorBowen Wang
State Key Laboratory of Pulp and Paper Engineering, Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, Guangdong, 510641 China
Search for more papers by this authorJianxiao Li
State Key Laboratory of Pulp and Paper Engineering, Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, Guangdong, 510641 China
Search for more papers by this authorWanqing Wu
State Key Laboratory of Pulp and Paper Engineering, Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, Guangdong, 510641 China
Search for more papers by this authorCorresponding Author
Huanfeng Jiang
State Key Laboratory of Pulp and Paper Engineering, Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, Guangdong, 510641 China
E-mail: [email protected]Search for more papers by this authorDedicated to the Memory of Professor Xiyan Lu.
Comprehensive Summary
Palladium-catalyzed regioselective amination of unactivated alkene remains a challenge and is of great interest. Herein, a three-component coupling of unactivated alkene, sulfonamide, and N-halo compounds accessing vicinal haloamine has been conceived. This aminohalogenation represents a modular and regioselective strategy. The electrophilic halogenating agent enables regioselective anti-Markovnikov aminopalladation and facilitates subsequent halogenation events. And this protocol is characterized by gram-scale syntheses and late-stage functionalizations. Of note, the recovered byproduct phthalimide allows for reusing by conversion to the starting material.
Supporting Information
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