Photocatalytic [3+2] Cycloaddition of Alkyl/aryl Iodides and Internal Alkynes by Merging Halogen and Hydrogen Atom Transfer
Zhenyu Gu
Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, College of Chemistry and Materials Science, Zhejiang Normal University, 688 Yingbin Road, Jinhua, Zhejiang, 321004 China
Search for more papers by this authorRong Jia
Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, College of Chemistry and Materials Science, Zhejiang Normal University, 688 Yingbin Road, Jinhua, Zhejiang, 321004 China
Search for more papers by this authorTianqing Zeng
Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, College of Chemistry and Materials Science, Zhejiang Normal University, 688 Yingbin Road, Jinhua, Zhejiang, 321004 China
Search for more papers by this authorCorresponding Author
Hanliang Zheng
Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, College of Chemistry and Materials Science, Zhejiang Normal University, 688 Yingbin Road, Jinhua, Zhejiang, 321004 China
E-mail: [email protected], [email protected]Search for more papers by this authorCorresponding Author
Gangguo Zhu
Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, College of Chemistry and Materials Science, Zhejiang Normal University, 688 Yingbin Road, Jinhua, Zhejiang, 321004 China
E-mail: [email protected], [email protected]Search for more papers by this authorZhenyu Gu
Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, College of Chemistry and Materials Science, Zhejiang Normal University, 688 Yingbin Road, Jinhua, Zhejiang, 321004 China
Search for more papers by this authorRong Jia
Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, College of Chemistry and Materials Science, Zhejiang Normal University, 688 Yingbin Road, Jinhua, Zhejiang, 321004 China
Search for more papers by this authorTianqing Zeng
Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, College of Chemistry and Materials Science, Zhejiang Normal University, 688 Yingbin Road, Jinhua, Zhejiang, 321004 China
Search for more papers by this authorCorresponding Author
Hanliang Zheng
Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, College of Chemistry and Materials Science, Zhejiang Normal University, 688 Yingbin Road, Jinhua, Zhejiang, 321004 China
E-mail: [email protected], [email protected]Search for more papers by this authorCorresponding Author
Gangguo Zhu
Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, College of Chemistry and Materials Science, Zhejiang Normal University, 688 Yingbin Road, Jinhua, Zhejiang, 321004 China
E-mail: [email protected], [email protected]Search for more papers by this authorComprehensive Summary
A visible light photocatalytic [3+2] cycloaddition of alkynes with readily accessible organic iodides as the C3 synthon is developed herein. By merging halogen atom transfer (XAT) and hydrogen atom transfer (HAT), alkyl/aryl iodides serve as a formal diradical precursor and add across C-C triple bonds to deliver a number of functionalized cyclopentanes in moderate to high yields with exceptional regio- and diastereoselectivity. A reductive radical-polar crossover mechanism, involving the cascade XAT, radical addition, 1,5-HAT, polar effect-promoted 5-endo annulation, single electron transfer (SET) reduction, and protonation, may account for this unprecedented dehalogenative [3+2] cycloaddition. This work not only expands the repertoire of the traditional RATC methodology, but also provides a robust platform for the expedient assembly of cyclopentanes, a valuable structural motif in the realms of medicinal chemistry and material sciences.
Supporting Information
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